Pesticidal mixtures comprising a pyrazole compound

ABSTRACT

The present invention relates to pesticidal mixtures comprising as active compounds
     1) at least one pyrazole compound A selected from the compounds of formula I:   

     
       
         
         
             
             
         
       
         
         
           
             wherein the variables have the meaning as defined in the description, and 
           
         
         2) at least one further compound B selected from the compounds of the following groups A.1, A.2, A.3, A.4, A.5, A.6, A.7, A.8, A.9, A.10, A.11, A.12, A.13, A.14, A.15, A.16, A.17, F.1, F.2, F.3, F.4, F.5, F.6, F.7, F.8, F.9, F.10 and F.11 as defined in the specification. 
       
    
     The present invention also relates to novel pyrazole compounds of the formula I. The present invention also relates to methods and use of these mixtures and novel compounds for combating invertebrate pests such as insects, arachnids or nematodes in and on plants, and for protecting such plants being infested with pests, especially also for protecting plant propagation material as like seeds.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a continuation of U.S. application Ser. No. 14/408,174, filed Dec. 15, 2014, the entire contents of which is hereby incorporated herein by reference. U.S. application Ser. No. 14/408,174 is a National Stage application of International Application No. PCT/EP2013/062123, filed Jun. 12, 2013. U.S. application Ser. No. 14/408,174 claims the benefit of U.S. Provisional Application No. 61/661,817, filed Jun. 20, 2012, and U.S. Provisional Application No. 61/717,117, filed Oct. 23, 2012, the entire contents of which are hereby incorporated herein by reference.

The present invention relates to a pesticidal mixture comprising as active compounds at least one pyrazole compound and at least one further pesticide and to novel pyrazole compounds. Furthermore, the invention relates to methods of applying said mixture or said pyrazole compound.

The present invention thus relates to pesticidal mixtures comprising as active compounds

-   1) at least one pyrazole compound A selected from the compounds of     formula I:

wherein

-   R¹ is H, C₁-C₂-alkyl, or C₁-C₂-alkoxy-C₁-C₂-alkyl; -   R² is CH₃, CH₂F, CHF₂, or CF₃; -   R³ is C₂-C₆-alkyl, a radical R^(3a) or a radical R^(3b); -   R⁴ is C₁-C₄-alkyl, or a group mentioned for R^(3a); -   R⁵ is H, halogen, or a group mentioned for R⁴; -   R³ and R⁴ together with the carbon atom, to which they are attached,     may form a monocyclic three- to six-membered carbo- or heterocycle,     which may contain 1 or 2 heteroatom moieties selected from N—R^(c),     0, and S(O)_(k), with k being 0, 1 or 2, which monocyclic three- to     six-membered carbo- or heterocycle is unsubstituted or may be     substituted by 1, 2, 3 or 4 radicals R^(a3); -   R³ and R⁴ together with the carbon atom, to which they are attached,     may also form a monospiro or dispiro 5- to 10-membered carbo- or     heterocycle, which may contain 1 or 2 heteroatom moieties selected     from N—R^(c), 0, and S(O)_(k), with k being 0, 1 or 2, which     monospiro or dispiro 5- to 10-membered carbo- or heterocycle is     unsubstituted or may be substituted by 1, 2, 3 or 4 radicals R^(a3);     -   R^(3a) is selected from the group consisting of CN, NO₂,         S(O)R^(b), C₁-C₄-haloalkyl, C₁-C₄-alkyl which is partially or         fully substituted by R^(a1), C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-alkoxy, wherein the C-atoms in the last 3 mentioned         radicals may be unsubstituted, or partially or fully substituted         by R^(a2), C₃-C₆-cycloalkyl and C₅-C₆-cycloalkenyl wherein the         C-atoms in the last 2 mentioned radicals may be unsubstituted,         or partially or fully substituted by R^(a3),     -   R^(3b) is a monospiro or dispiro 5- to 10-membered carbo- or         heterocycle, which may contain 1 or 2 heteroatom moieties         selected from N—R^(c), O, and S(O)_(k), with k being 0 1 or 2,         which monospiro or dispiro 5 to 10-membered carbo- or         heterocycle is unsubstituted or may be substituted by 1, 2, 3 or         4 radicals R^(a3);         -   R^(a1) is CN, NO₂, C(O)NH₂, C(S)NH₂, C₁-C₂-alkylcarbonyloxy,             C₁-C₄-alkoxy, C₁-C₂-haloalkoxy, C₁-C₂-alkyloxycarbonyl, or             S(O)_(n)R^(b);         -   R^(a2) is halogen, or a group mentioned for R^(a1);             -   R^(a3) is halogen, C₁-C₂-alkyl, C₁-C₂-haloalkyl,                 C₁-C₂-alkoxy-C₁-C₂-alkyl, C₁-C₂-alkyliden, ═O, ═S,                 ═NR^(b), ═NOR^(b), ═NSR^(b), or a group mentioned for                 R^(a1), in particular halogen, C₁-C₂-alkyl,                 C₁-C₂-alkoxy-C₁-C₂-alkyl, C₁-C₂-alkyliden, or a group                 mentioned for R^(a1); n is 0, 1, or 2;             -   R^(b) is hydrogen, C₁-C₂-alkyl, C₁-C₂-haloalkyl,                 C₃-C₆-cycloalkyl, or C₁-C₄-alkoxy;             -   R^(c) is hydrogen, C₁-C₂-alkyl, C₁-C₂-haloalkyl,                 C₁-C₂-alkylcarbonyl, or C₁-C₂-alkoxycarbonyl;                 the stereoisomers, salts, tautomers and N-oxides                 thereof; and -   2) at least one further compound B selected from the compounds of     the following groups A.1, A.2, A.3, A.4, A.5, A.6, A.7, A.8, A.9,     A.10, A.11, A.12, A.13, A.14, A.15, A.16, A.17, F.1, F.2, F.3, F.4,     F.5, F.6, F.7, F.8, F.9, F.10 and F.11: -   A.1 Carbamate compounds, selected from the group consisting of     methiocarb and thiodicarb; -   A.2 Pyrethroid compounds, selected from the group consisting of     acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin,     bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl,     bio-resmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin,     cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin,     alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin,     zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin,     esfenvalerate, etofenprox, fenpropathrin, fenvalerate,     flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin,     meperfluthrin, metofluthrin, permethrin, phenothrin, prallethrin,     profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen,     tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and     transfluthrin; -   A.3 Nicotinic receptor agonists/antagonists compounds, selected from     the group consisting of acetamiprid, bensultap, cartap     hydrochloride, clothianidin, dinotefuran, imidacloprid,     thiamethoxam, nitenpyram, spinosad (allosteric agonist), spinetoram     (allosteric agonist), thiacloprid, thiocyclam and thiosultap-sodium -   A.4 GABA gated chloride channel antagonist compounds, selected from     the group consisting of acetoprole, ethiprole and fipronil; -   A.5 Chloride channel activators, selected from the group consisting     of abamectin, emamectin benzoate, milbemectin and lepimectin; -   A.6 Uncouplers of oxidative phosphorylation, namely chlorfenapyr; -   A.7 Synergists, namely piperonyl butoxide; -   A.8 Selective feeding blockers, selected from the group consisting     of pymetrozine and flonicamid; -   A.9 Chitin synthesis inhibitors, selected from the group consisting     of teflubenzuron and novaluron; -   A.10 Lipid biosynthesis inhibitors, selected from the group     consisting of spirodiclofen, spiromesifen and spirotetramat; -   A.11 Diamide-type Ryanodine receptor modulators—Phthalamides,     selected from the group consisting of flubendiamide and (R)-,     (S)-3-chloro-N1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N2-(1-methyl-2-methylsulfonylethyl)phthalamide     (A11.1); -   A.12 Isoxazoline compounds, selected from the group consisting of     4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-pyridin-2-ylmethyl-benzamide     (A12.1),     4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-(2,2,2-trifluoroethyl)-benzamide     (A12.2),     4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide     (A12.3),     4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalene-1-carboxylic     acid [(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-amide (A12.4),     4-[5-(3-chloro-5-trifluoromethyl-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-methyl-N-[(2,2,2-trifluoro-ethylcarbamoyl)-methyl]-benzamide     (A12.5),     4-[5-(3-chloro-5-trifluoromethylphenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-naphthalene-1-carboxylic     acid [(2,2,2-trifluoroethylcarbamoyl)-methyl]-amide (A12.6),     5-[5-(3,5-dichloro-4-fluorophenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-[1,2,4]triazol-1-yl-benzonitrile     (A12.7) and     5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-2-[1,2,4]triazol-1-yl-benzonitrile     (A12.8); -   A.13 Diamide-type Ryanodine receptor modulators—Anthranilamide     compounds, selected from the group consisting of     chloranthraniliprole (rynaxypyr), cyantraniliprole,     5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic acid     [4-cyano-2-(1-cyclopropyl-ethylcarbamoyl)-6-methyl-phenyl]-amide     (A13.1), 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic     acid     [2-chloro-4-cyano-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide     (A13.2), 5-bromo-2-(3-chloropyridin-2-yl)-2H-pyrazole-3-carboxylic     acid [2-bromo-4-cyano-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide     (A13.3), 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic     acid     [2-bromo-4-chloro-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]-amide     (A13.4), 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic     acid [2,4-dichloro-6-(1-cyclopropyl-ethylcarbamoyl)-phenyl]amide     (A13.5), 5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carboxylic     acid     [4-chloro-2-(1-cyclopropyl-ethylcarbamoyl)-6-methyl-phenyl]amide     (A13.6),     N′-(2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3-methyl-benzoyl)-hydrazinecarboxylic     acid methyl ester (A13.7),     N′-(2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3-methyl-benzoyl)-W-methyl-hydrazinecarboxylic     acid methyl ester (A13.8),     N′-(2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-5-chloro-3-methyl-benzoyl)-N,N′-dimethyl-hydrazinecarboxylic     acid methyl ester (A13.9),     N′-(3,5-dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-benzoyl)-hydrazinecarboxylic     acid methyl ester (A13.10),     N′-(3,5-dibromo-2-{[5-bromo-2-(3-chloro-pyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-benzoyl)-N′-methyl-hydrazine     carboxylic acid methyl ester (A13.11) and     N′-(3,5-dibromo-2-{[5-bromo-2-(3-chloropyridin-2-yl)-2H-pyrazole-3-carbonyl]-amino}-benzoyl)-N,N′-dimethyl-hydrazinecarboxylic     acid methyl ester (A13.12); -   A.14 Malononitrile compounds, selected from the group consisting of     2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,3-trifluoropropyl)     malononitrile (CF₂H—CF₂—CF₂—CF₂—CH₂—C(CN)₂—CH₂—CH₂—CF₃) (A14.1) and     2-(2,2,3,3,4,4,5,5-octafluoropentyl)-2-(3,3,4,4,4-pentafluorobutyl)-malonodinitrile     (CF₂HCF₂—CF₂—CF₂—CH₂—C(CN)₂—CH₂—CH₂—CF₂—CF₃) (A14.2); -   A.15 Microbial disruptors, selected from the group consisting of     Bacillus thuringiensis subsp. Israelensi, Bacillus sphaericus,     Bacillus thuringiensis subsp. Aizawai, Bacillus thuringiensis subsp.     Kurstaki and Bacillus thuringiensis subsp. Tenebrionis; -   A.16 Aminofuranone compounds, selected from the group consisting of     4-{[(2-chloro1,3-thiazolo-5-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on     (A16.1),     4-{[(6-chloropyrid-3-yl)methyl](2-fluoroethyl)amino}furan-2(5H)-on     (A16.2),     4-{[(6-chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-on     (A16.3),     4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on     (A16.4),     4-{[(6-chloro-5-fluoropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on     (A16.5),     4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on     (A16.6) and     4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (A16.7); -   A.17 Various compounds, selected from the group consisting of     aluminium phosphide, amidoflumet, benclothiaz, benzoximate,     bifenazate, borax, bromopropylate, cryolite, cyanide, cyenopyrafen,     cyflumetofen, chinomethionate, dicofol, fluensulfone, fluoroacetate,     phosphine, pyridalyl, pyrifluquinazon, sulfur, organic sulfur     compounds, tartar emetic, sulfoxaflor, afidopyropen     (cyclopropaneacetic acid,     1,1′-[(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-cyclopropylacetyl)oxy]methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-3,6-diyl]ester),     4-but-2-ynyloxy-6-(3,5-dimethyl-piperidin-1-yl)-2-fluoro-pyrimidine     (A17.1), and     8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane     (A17.2). -   F.1 Respiration inhibitors selected from the following groups a),     b), c) and d):     -   a) Inhibitors of complex III at Q_(o) site (e.g. strobilurins),         selected from the group consisting of azoxystrobin,         coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin,         fenaminstrobin, fenoxystrobin/flufenoxystrobin, fluoxastrobin,         kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin,         pyraclostrobin, pyrametostrobin, pyraoxystrobin,         trifloxystrobin,         2-[2-(2,5-dimethyl-phenoxymethyl)-phenyl]-3-methoxy-acrylic acid         methyl ester and         2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide,         pyribencarb, triclopyricarb/chlorodincarb, famoxadone and         fenamidone;     -   b) inhibitors of complex III at Q site, selected from the group         consisting of cyazofamid and amisulbrom;     -   c) inhibitors of complex II (e.g. carboxamides), selected from         the group consisting of benodanil, bixafen, boscalid, carboxin,         fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr,         isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad,         sedaxane, tecloftalam, thifluzamide,         N-(4′-trifluoromethylthiobiphenyl-2-yl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide         and         N-(2-(1,3,3-trimethyl-butyl)-phenyl)-1,3-dimethyl-5-fluoro-1H-pyrazole-4-carboxamide;     -   d) other respiration inhibitors (e.g. complex I, uncouplers),         selected from the group consisting of diflumetorim; the         nitrophenyl derivatives: binapacryl, dinobuton, dinocap and         fluazinam; ferimzone; fentin salts, such as fentin-acetate,         fentin chloride or fentin hydroxide; ametoctradin; and         silthiofam; -   F.2 Sterol biosynthesis inhibitors (SBI fungicides) selected from     the following groups a), b) and c):     -   a) C14 demethylase inhibitors (DMI fungicides), selected from         the group consisting of the following triazoles: azaconazole,         bitertanol, bromuconazole, cyproconazole, difenoconazole,         diniconazole, diniconazole-M, epoxiconazole, fenbuconazole,         fluquinconazole, flusilazole, flutriafol, hexaconazole,         imibenconazole, ipconazole, metconazole, myclobutanil,         oxpoconazole, paclobutrazole, penconazole, propiconazole,         prothioconazole, simeconazole, tebuconazole, tetraconazole,         triadimefon, triadimenol, triticonazole and uniconazole; the         following imidazoles: imazalil, pefurazoate, prochloraz and         triflumizol; and the following pyrimidines, pyridines and         piperazines: fenarimol, nuarimol, pyrifenox and triforine;     -   b) Delta14-reductase inhibitors, selected from the group         consisting of aldimorph, dodemorph, dodemorph-acetate,         fenpropimorph, tridemorph, fenpropidin, piperalin and         spiroxamine;

c) Inhibitors of 3-keto reductase: fenhexamid;

-   F.3 Nucleic acid synthesis inhibitors selected from the following     groups a) and b):

a) phenylamides or acyl amino acid fungicides, selected from the group consisting of benalaxyl, benalaxyl-M, kiralaxyl, metalaxyl, metalaxyl-M (mefenoxam), ofurace and oxadixyl;

-   -   b) other nucleic acid synthesis inhibitors, selected from the         group consisting of hymexazole, octhilinone, oxolinic acid and         bupirimate;

-   F.4 Inhibitors of cell division and cytoskeleton selected from the     following groups a) and b):     -   a) tubulin inhibitors, selected from the group consisting of         benzimidazoles or thiophanates such as benomyl, carbendazim,         fuberidazole, thiabendazole or thiophanate-methyl; and         triazolopyrimidines such as         5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine;     -   b) other cell division inhibitors, selected from the group         consisting of diethofencarb, ethaboxam, pencycuron,         fluopicolide, zoxamide, metrafenone and pyriofenone;

-   F.5 Inhibitors of amino acid and protein synthesis selected from the     following groups a) and b):     -   a) methionine synthesis inhibitors (anilino-pyrimidines),         selected from the group consisting of cyprodinil, mepanipyrim         and pyrimethanil;     -   b) protein synthesis inhibitors, selected from the group         consisting of blasticidin-S, kasugamycin, kasugamycin         hydrochloride-hydrate, mildiomycin, streptomycin,         oxytetracyclin, polyoxine and validamycin A;

-   F.6 Signal transduction inhibitors selected from the following     groups a) and b):     -   a) MAP/histidine kinase inhibitors, selected from the group         consisting of fluoroimid, iprodione, procymidone, vinclozolin,         fenpiclonil and fludioxonil;     -   b) G protein inhibitors which is quinoxyfen;

-   F.7 Lipid and membrane synthesis inhibitors selected from the     following groups a), b), c) and d):     -   a) Phospholipid biosynthesis inhibitors, selected from the group         consisting of edifenphos, iprobenfos, pyrazophos and         isoprothiolane;     -   b) compounds affecting lipid peroxidation, selected from the         group consisting of dicloran, quintozene, tecnazene,         tolclofos-methyl, biphenyl, chloroneb and etridiazole;     -   c) compounds affecting phospholipid biosynthesis and cell wall         deposition, selected from the group consisting of dimethomorph,         flumorph, mandipropamid, pyrimorph, benthiavalicarb,         iprovalicarb, valifenalate and         N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic         acid-(4-fluorophenyl) ester;     -   d) compounds affecting cell membrane permeability and fatty         acids selected from the group consisting of propamocarb and         propamocarb-hydrochlorid;

-   F.8 Inhibitors with multi site action selected from the following     groups a), b), c) and d):     -   a) inorganic active substances selected from the group         consisting of Bordeaux mixture, copper acetate, copper         hydroxide, copper oxychloride, basic copper sulfate and sulfur;     -   b) thio- and dithiocarbamates selected from the group consisting         of ferbam, mancozeb, maneb, metam, metiram, propineb, thiram,         zineb and ziram;     -   c) organochlorine compounds (e.g. phthalimides, sulfamides,         chloronitriles) selected from the group consisting of anilazine,         chlorothalonil, captafol, captan, folpet, dichlofluanid,         dichlorophen, flusulfamide, hexachlorobenzene, pentachlorphenole         and its salts, phthalide, tolylfluanid and         N-(4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl-benzenesulfonamide;     -   d) guanidines and others selected from the group consisting of         guanidine, dodine, dodine free base, guazatine,         guazatine-acetate, iminoctadine, iminoctadine-triacetate,         iminoctadine-tris(albesilate) and dithianon;

-   F.9 Cell wall synthesis inhibitors selected from the following     groups a) and b):     -   a) inhibitors of glucan synthesis selected from the group         consisting of validamycin and polyoxin B;     -   b) melanin synthesis inhibitors selected from the group         consisting of pyroquilon, tricyclazole, carpropamid, dicyclometa         and fenoxanil;

-   F.10 Plant defence inducers selected from the following groups a)     and b):     -   a) the group of acibenzolar-S-methyl, probenazole, isotianil,         tiadinil and prohexadione-calcium;     -   b) phosphonates selected from the group consisting of fosetyl,         fosetyl-aluminum, phosphorous acid and its salts;

-   F.11 Fungicides having an unknown mode of action selected from the     group consisting of bronopol, chinomethionat, cyflufenamid,     cymoxanil, dazomet, debacarb, diclomezine, difenzoquat,     difenzoquat-methylsulfate, diphenylamin, fenpyrazamine, flumetover,     flusulfamide, flutianil, methasulfocarb, nitrapyrin,     nitrothal-isopropyl, oxin-copper, proquinazid, tebufloquin,     tecloftalam, triazoxide, 2-butoxy-6-iodo-3-propylchromen-4-one,     N-(cyclopropylmethoxyimino-(6-difluoro-methoxy-2,3-difluoro-phenyl)-methyl)-2-phenyl     acetamide,     N′-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-Nethyl-N-methyl     formamidine,     N′-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methyl     formamidine,     N′-(2-methyl-5-trifluoromethyl-4-(3-trimethyl-silanyl-propoxy)-phenyl)-N-ethyl-N-methyl     formamidine,     N′-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl     formamidine,     2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylic     acid methyl-(1,2,3,4-tetrahydronaphthalen-1-yl)-amide,     2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazole-1-yl)-acetyl]-piperidin-4-yl}thiazole-4-carboxylic     acid methyl-(R)-1,2,3,4-tetra-hydro-naphthalen-1-yl-amide,     methoxy-acetic acid 6-tert-butyl-8-fluoro-2,3-dimethylquinolin-4-yl     ester,     N-Methyl-2-{1-[(5-methyl-3-trifluoromethyl-1H-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-4-thiazolecarboxamide,     3-[5-(4-methyl-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,     3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]pyridine     (pyrisoxazole), N-(6-methoxy-pyridin-3-yl) cyclopropanecarboxylic     acid amide,     5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1Hbenzoimidazole,     2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide;

except for pesticidal mixtures comprising a pyrazole compound of formula I, wherein

R¹ is H, CH₃, C₂H₅, or CH₂OCH₃; R² is CH₃, CHF₂, or CF₃; R³ is CF₃, or c-C₃H₅; R⁴ is CH₃; and

R⁵ is H.

One typical problem arising in the field of pest control lies in the need to reduce the dosage rates of the active ingredient in order to reduce or avoid unfavorable environmental or toxicological effects whilst still allowing effective pest control. Another problem encountered concerns the need to have available pest control agents which are effective against a broad spectrum of pests.

Another problem underlying the present invention is the desire for compositions that improve plants, a process which is commonly and hereinafter referred to as “plant health”. For example, advantageous properties that may be mentioned are improved crop characteristics including: emergence, crop yields, protein content, more developed root system, tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf color, pigment content, photosynthetic activity, less fertilizers needed, less seeds needed, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, enhanced plant vigor, increased plant stand and early germination; or any other advantages familiar to a person skilled in the art. Methods for improving the health of plants by applying active compounds to the plants or the locus are a general need.

The combating of harmful phytopathogenic fungi is in many regions not the only problem the farmer has to face. Invertebrate pests and in particular arthropods and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, thereby causing large economic loss to the food supply and to property. There is an ongoing need for new agents for combating invertebrate pests such as insects, arachnids and nematodes. It is therefore an object of the present invention to provide compounds having a good pesticidal activity and showing a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to control pests, such as insects.

An efficient combination of fungicidal and insecticidal activity is also desirable. Thus, it is a further object of the present invention to provide a mixture which, on the one hand, has good fungicidal activity, and, on the other hand, good insecticidal activity, resulting in a broader pesticidal spectrum of action.

Another difficulty in relation to the use of pesticides is that the repeated and exclusive application of an individual pesticidal compound leads in many cases to a rapid selection of pests which have developed natural or adapted resistance against the active compound in question. Therefore there is a need for pest control agents that help prevent or overcome resistance.

WO 2009/027393, WO 2010/034737, WO 2010/034738, and WO 2010/112177 describe derivatives of N-(het)arylamides, derived from pyrazole carboxylic acids. These compounds are mentioned to be useful for combating invertebrate pests.

PCT/EP2012/056875 describes N-pyridazinyl carboxamide compounds derived from pyrazole carboxylic acids. These compounds are mentioned to be useful for combating invertebrate pests. However, this document does not describe compounds having the characteristic substituents as claimed in the present invention.

PCT/EP2011/072854 relates to pesticidal mixtures comprising N-pyridazinyl carboxamide compounds derived from pyrazole carboxylic acids. These compounds are mentioned to be useful for combating invertebrate pests and/or for controlling phytopathogenic harmful fungi. However, this document does not describe N-pyridazinyl carboxamide compounds having the characteristic substituents as claimed in the present invention.

It is therefore an object of the present invention to provide pesticidal mixtures and/or compounds which solves at least one of the discussed problems as reducing the dosage rate, enhancing the spectrum of activity or combining knock-down activity with prolonged control or as to resistance management.

It as been found that at least one of these objectives is achieved by the combination of active compounds defined in the outset or by the pyrazole compounds defined below.

Moreover, it has also been found that simultaneous, that is joint or separate, application of one or more active compounds A and one or more active compounds B or successive application of one or more active compounds A and one or more active compounds B allows enhanced control of pests compared to the control rates that are possible with the individual compounds.

The present invention also relates to novel pyrazole compounds of the formula I (hereinafter compounds I-S):

wherein

-   R¹ is H, C₁-C₂-alkyl, or C₁-C₂-alkoxy-C₁-C₂-alkyl; -   R² is CH₃, CH₂F, CHF₂, or CF₃; -   R³ is a radical R^(3b), -   R⁴ is C₁-C₄-alkyl, or a radical R^(3a);     -   R^(3a) is selected from the group consisting of CN, NO₂,         S(O)R^(b), C₁-C₄-haloalkyl, C₁-C₄-alkyl which is partially or         fully substituted by R^(a1), C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-alkoxy, wherein the C-atoms in the last 3 mentioned         radicals may be unsubstituted, or partially or fully substituted         by R^(a2), C₃-C₆-cycloalkyl and C₅-C₆-cycloalkenyl wherein the         C-atoms in the last 2 mentioned radicals may be unsubstituted,         or partially or fully substituted by R^(a3),     -   R^(3b) is a monospiro or dispiro 5- to 10-membered carbo- or         heterocycle, which may contain 1 or 2 heteroatom moieties         selected from N—R^(c), O, and S(O)_(k), with k being 0 1 or 2,         which monospiro or dispiro 5- to 10-membered carbo- or         heterocycle is unsubstituted or may be substituted by 1, 2, 3 or         4 radicals R^(a3);         -   R^(a1) is CN, NO₂, C(O)NH₂, C(S)NH₂, C₁-C₂-alkylcarbonyloxy,             C₁-C₄-alkoxy, C₁-C₂-haloalkoxy, C₁-C₂-alkyloxycarbonyl, or             S(O)_(n)R^(b);         -   R^(a2) is halogen, or a group mentioned for R^(a1);         -   R^(a3) is halogen, C₁-C₂-alkyl, C₁-C₂-haloalkyl,             C₁-C₂-alkoxy-C₁-C₂-alkyl, C₁-C₂-alkyliden, ═O, ═S, ═NR^(b),             ═NOR^(b), ═NSR^(b), or a group mentioned for R^(a1); in             particular halogen, C₁-C₂-alkyl, C₁-C₂-alkoxy-C₁-C₂-alkyl,             C₁-C₂-alkyliden, or a group mentioned for R^(a1);         -   n is 0, 1, or 2;             -   R^(b) is H, C₁-C₂-alkyl, C₁-C₂-haloalkyl,                 C₃-C₆-cycloalkyl, or C₁-C₄-alkoxy,             -   R^(c) is H, C₁-C₂-alkyl, C₁-C₂-haloalkyl,                 C₁-C₂-alkylcarbonyl, or C₁-C₂-alkoxycarbonyl; -   R⁵ is H, halogen, or a group mentioned for R⁴; -   the stereoisomers, salts, tautomers and N-oxides thereof.

The present invention also relates to novel pyrazole compounds of the formula I (hereinafter compounds I-S),

wherein

-   R¹ is H, C₁-C₂-alkyl, or C₁-C₂-alkoxy-C₁-C₂-alkyl; -   R² is CH₃, CH₂F, CHF₂ or CF₃; -   R³ and R⁴ together with the carbon atom, to which they are attached,     form a monospiro or dispiro 5 to 10-membered carbo- or heterocycle,     which may contain 1 or 2 heteroatom moieties selected from N—R^(c),     O, and S(O)_(k), with k being 0 1 or 2, which monospiro or dispiro 5     to 10-membered carbo- or heterocycle is unsubstituted or may be     substituted by 1, 2, 3 or 4 radicals R^(a3);     -   R^(3a) is selected from the group consisting of CN, NO₂,         S(O)R^(b), C₁-C₄-haloalkyl, C1-C4-alkyl which is partially or         fully substituted by R^(a1), C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-alkoxy, wherein the C-atoms in the last 3 mentioned         radicals may be unsubstituted, or partially or fully substituted         by R^(a2), C₃-C₆-cycloalkyl and C₅-C₆-cycloalkenyl wherein the         C-atoms in the last 2 mentioned radicals may be unsubstituted,         or partially or fully substituted by R^(a3),         -   R^(a1) is CN, NO₂, C(O)NH₂, C(S)NH₂, C₁-C₂-alkylcarbonyloxy,             C₁-C₄-alkoxy, C₁-C₂-haloalkoxy, C₁-C₂-alkyloxycarbonyl, or             S(O)_(n)R^(b);         -   R^(a2) is halogen, or a group mentioned for R^(a1);         -   R^(a3) is halogen, C₁-C₂-alkyl, C₁-C₂-haloalkyl,             C₁-C₂-alkoxy-C₁-C₂-alkyl, C₁-C₂-alkyliden, ═O, ═S, ═NR^(b),             ═NOR^(b), ═NSR^(b), or a group mentioned for R^(a1); in             particular halogen, C₁-C₂-alkyl, C₁-C₂-alkoxy-C₁-C₂-alkyl,             C₁-C₂-alkyliden, or a group mentioned for R^(a1);             -   n is 0, 1, or 2;             -   R^(b) is H, C₁-C₂-alkyl, C₁-C₂-haloalkyl,                 C₃-C₆-cycloalkyl, or C₁-C₄-alkoxy,             -   R^(c) is H, C₁-C₂-alkyl, C₁-C₂-haloalkyl,                 C₁-C₂-alkylcarbonyl, or C₁-C₂-alkoxycarbonyl; -   R⁵ is H, halogen, C₁-C₄-alkyl, or a group mentioned for R^(3a); -   the stereoisomers, salts, tautomers and N-oxides thereof.

The present invention also relates to novel pyrazole compounds of the formula I (hereinafter compounds 1-0), wherein

-   R¹ is H, C₁-C₂-alkyl, or C₁-C₂-alkoxy-C₁-C₂-alkyl; -   R² is CH₃, CH₂F, CHF₂, or CF₃; -   R³ and R⁴ together with the carbon atom, to which they are attached,     may form a monocyclic three- to six-membered carbo- or heterocycle,     which may contain 1 or 2 heteroatom moieties selected from N—R^(c),     O, and S(O)_(k), with k being 0, 1 or 2, which carbo- or heterocycle     is substituted by 1, 2, or 3 groups ═O, ═S, ═NR^(b), ═NOR^(b),     ═NSR^(b), and may be substituted by 1, 2, 3 or 4 radicals R^(a33); -   R³ and R⁴ together with the carbon atom, to which they are attached,     may also form a monospiro or dispiro 5- to 10-membered carbo- or     heterocycle, which may contain 1 or 2 heteroatom moieties selected     from N—R^(c), O, and S(O)_(k), with k being 0, 1 or 2, which     monospiro or dispiro 5- to 10-membered carbo- or heterocycle is     unsubstituted or may be substituted by 1, 2, 3 or 4 radicals R^(a3);     -   R^(3a) is selected from the group consisting of CN, NO₂,         S(O)R^(b), C₁-C₄-haloalkyl, C₁-C₄-alkyl which is partially or         fully substituted by R^(a1), C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₁-C₆-alkoxy, wherein the C-atoms in the last 3 mentioned         radicals may be unsubstituted, or partially or fully substituted         by R^(a2), C₃-C₆-cycloalkyl and C₅-C₆-cycloalkenyl wherein the         C-atoms in the last 2 mentioned radicals may be unsubstituted,         or partially or fully substituted by R^(a3),         -   R^(a1) is CN, NO₂, C(O)NH₂, C(S)NH₂, C₁-C₂-alkylcarbonyloxy,             C₁-C₄-alkoxy, C₁-C₂-haloalkoxy, C₁-C₂-alkyloxycarbonyl, or             S(O)_(n)R^(b);         -   n is 0, 1, or 2;         -   R^(a2) is halogen, or a group mentioned for R^(a1);         -   R^(a33) is halogen, C₁-C₂-alkyl, C₁-C₂-haloalkyl,             C₁-C₂-alkoxy-C₁-C₂-alkyl, C₁-C₂-alkyliden or a group             mentioned for R^(a1);         -   R^(b) is H, C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₃-C₆-cycloalkyl,             or C₁-C₄-alkoxy;         -   R^(c) is H, C₁-C₂-alkyl, C₁-C₂-haloalkyl,             C₁-C₂-alkylcarbonyl, or C₁-C₂-alkoxycarbonyl; -   R⁵ is H, C₁-C₄-alkyl, halogen, or a group mentioned for R^(3a); -   the stereoisomers, salts, tautomers and N-oxides thereof.

The present invention also relates to novel pyrazole compounds of the formula I which are selected from the compounds of the following groups I-a, I-b, I-c, and I-d:

Compounds of group I-a: Compounds of the formula I, wherein:

-   R¹ is H, C₁-C₂-alkyl, or C₁-C₂-alkoxy-C₁-C₂-alkyl, in particular     CH₃, or C₂H₅; -   R² is CH₃, CH₂F, CHF₂ or CF₃; -   R³ is CN, CH(CH₃)₂, CHF₂, CH₂OCH₃, c-C₃H₅, 1-F-c-C₃H₄, or     1-CN-c-C₃H₄; -   R⁴ is CHF₂; -   R⁵ is H, or CH₃; -   the stereoisomers, salts, tautomers and N-oxides thereof; -   except for the following pyrazole compounds of the group I-a, where     in formula I -   R¹ is CH₃, or C₂H₅; R² is CH₃, CHF₂ or CF₃; R³ is CN; R⁴ is CHF₂;     and R⁵ is CH₃.

Compounds of group I-b: Compounds of the formula I, wherein:

-   R¹ is H, C₁-C₂-alkyl, or C₁-C₂-alkoxy-C₁-C₂-alkyl, in particular CH₃     or C₂H₅; -   R² is CH₃, CH₂F, CHF₂ or CF₃; -   R³ is selected from the group consisting of     -   1-CH₃-c-C₃H₄, 1-OCH₃-c-C₃H₄, 1-CF₃-c-C₃H₄, 1-OCF₃-c-C₃H₄,         1-SCH₃-c-C₃H₄, 1-SCF₃-c- C₃H₄, C(CH₃)₃, 1-F-1-methylethyl,         1-CN-1-methylethyl, 1-methoxy-1-methylethyl,         1-(trifluoromethoxy)-1-methylethyl,         1-(methylsulfanyl)-1-methylethyl,         1-(trifluoromethylsulfanyl)-1-methylethyl,         2,2,2-trifluoro-1,1-dimethylethyl, CHFCH₃, CH(CN)CH₃, CF₂CH₃,         1,1-dimethoxyethyl, 1-methoxyethyl, 1-(trifluoromethoxy)-ethyl,         1-(methylsulfanyl)ethyl, 1-(trifluoromethylsulfanyl)ethyl,         2,2,2-trifluoro-1-methylethyl, CH₂SCH₃, CH₂SCF₃, CH₂OCF₃, CH₂F,         CH₂CF₃ and CH₂CN, R⁴ is CH₃, C₂H₅, CHF₂, or CF₃; -   R⁵ is H, or CH₃; -   the stereoisomers, salts, tautomers and N-oxides thereof; -   except for the following pyrazole compounds of the group I-b, where     in formula I -   R¹ is CH₃; R² is CF₃; R³ is C(CH₃)₃; R⁴ is CH₃; and R⁵ is H; -   and also except for the following pyrazole compounds of the group     I-b where in formula I the variable R¹ is CH₃ or C₂H₅; R² is CH₃; R³     is C(CH₃)₃, CH₂CN, CH₂F, CHFCH₃, 1-CH₃-c-C₃H₄, 1-CN-1-methylethyl,     1-SCH₃-c-C₃H₄, or 1-(CF₃)cyclopropyl; -   R⁴ is CH₃; and R⁵ is H; -   and also except for the following pyrazole compounds of the group     I-b where in formula I R¹ is H, CH₃, CH₂CH₃, or CH₂OCH₃; R² is CH₃     or CF₃; R³ is C(CH₃)₃, CH₂CN, CH₂F, CHFCH₃, 1-CH₃-cC₃H₄, C(CH₃)₂CN,     CH₂CF₃, 1-(SCH₃)-cC₃H₄, or 1-CF₃-cC₃H₄; R⁴ is CH₃ or CF₃; and R⁵ is     H; -   and exceptionally except within the last mentioned group the     following pyrazole compounds of the group I-b where in formula I R¹,     R², R³, R⁴ and R⁵ have the meaning as listed in the following table:

R¹ R² R³ R⁴ R⁵ H CH₃ C(CH₃)₃ CH₃ H CH₂OCH₃ CH₃ C(CH₃)₃ CH₃ H H CF₃ C(CH₃)₃ CH₃ H CH₂OCH₃ CF₃ C(CH₃)₃ CH₃ H H CH₃ CH₂CN CH₃ H CH₂OCH₃ CH₃ CH₂CN CH₃ H H CH₃ CH₂F CH₃ H H CH₃ CHFCH₃ CH₃ H H CH₃ 1-CH₃—cC₃H₄ CH₃ H H CH₃ C(CH₃)₂CN CH₃ H CH₂CH₃ CH₃ CH₂CF₃ CH₃ H H CH₃ CH₂CF₃ CH₃ H H CH₃ 1-(SCH₃)—cC₃H₄ CH₃ H CH₂CH₃ CH₃ C(CH₃)₃ CF₃ H CH₃ CH₃ C(CH₃)₃ CF₃ H H CH₃ C(CH₃)₃ CF₃ H H CH₃ 1-CH₃—cC₃H₄ CH₃ H H CH₃ 1-CF₃—cC₃H₄ CH₃ H

Compounds of group l-c: Compounds of the formula I, wherein:

-   R¹ is H, C₁-C₂-alkyl, or C₁-C₂-alkoxy-C₁-C₂-alkyl, in particular CH₃     or C₂H₅; -   R² is CH₃, CH₂F, CHF₂, or CF₃; -   R³ together with R⁴ forms a bivalent moiety (CH₂)_(p) with p being     2, 4, or 5; -   R⁵ is CH₃, F, OCH₃, SCH₃, OCF₃, or SCF₃; -   the stereoisomers, salts, tautomers and N-oxides thereof.

Compounds of group I-d: Compounds of the formula I, wherein:

-   R¹ is H, C₁-C₂-alkyl, or C₁-C₂-alkoxy-C₁-C₂-alkyl, in particular     CH₃, or C₂H₅; -   R² is CH₃, CH₂F, CHF₂ or CF₃; -   R³ together with R⁴ forms a bivalent moiety CH₂OCH₂OCH₂ or     CH₂OC(CH₃)₂OCH₂; -   R⁵ is H, CH₃, CN, F, OCH₃, SCH₃, CF₃, OCF₃, or SCF₃; -   the stereoisomers, salts, tautomers and N-oxides thereof.

Moreover, the present invention relates to

-   -   a composition comprising the pesticidal mixture as defined         herein or one novel compound of the formula I as defined herein         and at least one inert liquid and/or solid acceptable carrier;     -   an agricultural composition comprising the pesticidal mixture as         defined herein or a novel compound of the formula I as defined         herein and at least one inert liquid and/or solid acceptable         carrier;     -   a method for controlling or combating invertebrate pests,         comprising contacting said pest or its food supply, habitat,         breeding grounds with a pesticidally effective amount of the         pesticidal mixture as defined herein or with the novel compound         of the formula I as defined herein;     -   a method of protecting plants from attack or infestation by         invertebrate pests, contacting a plant, a plant propagation         material or soil or water in which the plant is growing, with a         pesticidally effective amount of the pesticidal mixture as         defined herein or with the novel pyrazole compound of the         formula I as defined herein;     -   a plant propagation material comprising the pesticidal mixture         as defined herein or the novel pyrazole compound of the formula         I as defined herein in an amount of from 0.1 g to 10 kg per 100         kg of seed;     -   a method for protection of plant propagation material comprising         contacting the plant propagation material with the pesticidal         mixture as defined herein or with a novel pyrazole compound of         the formula I as defined herein in an amount of from 0.1 g to 10         kg per 100 kg of plant propagation material;     -   the use of the pesticidal mixture as defined herein or of the         novel pyrazole compound of the formula I as defined herein for         protecting growing plants or plant propagation material from         attack or infestation by invertebrate pests;     -   a method for controlling phytopathogenic harmful fungi, wherein         the fungi, their habitat or the plants to be protected against         fungal attack, the soil or seed are treated with an effective         amount of the pesticidal mixture comprising at least one         pyrazole compound A as defined herein and at least one specific         compound B as defined herein;     -   a method for protecting plants from phytopathogenic harmful         fungi, wherein the fungi, their habitat or the plants to be         protected against fungal attack, the soil or seed are treated         with an effective amount of the pesticidal mixture comprising at         least one pyrazole compound A as defined herein and at least one         specific compound B as defined herein;     -   a method for protecting animals against infestation or infection         by parasites which comprises administering to the animals a         parasitically effective amount of the pesticidal mixture as         defined herein or of the novel pyrazole compound of the formula         I as defined herein;     -   a method for treating animals infested or infected by parasites         which comprises administering to the animals a parasitically         effective amount of the pesticidal mixture as defined herein or         of the novel pyrazole compound of the formula I as defined         herein to the animal in need thereof; and     -   the use of the pesticidal mixture as defined herein or of the         novel pyrazole compound of the formula I as defined herein for         combating parasites in and on animals.

The composition according to the invention or to be used according to the invention may be a physical mixture of the at least one compound A and the at least one compound B. Accordingly, the invention also provides a mixture comprising at least one compound A and at least one compound B. However, the composition may also be any combination of at least one compound A with at least one compound B, it not being required for compounds A and B to be present together in the same formulation.

An example of a composition according to the invention or to be used according to the invention in which the at least one compound A and the at least one compound B are not present together in the same formulation is a combipack. In a combipack, two or more components of a combipack are packaged separately, i.e., not jointly pre-formulated. As such, combipacks include one or more separate containers such as vials, cans, bottles, pouches, bags or canisters, each container containing a separate component for an agrochemical composition. One example is a two-component combipack. Accordingly the present invention also relates to a two-component combipack, comprising a first component which in turn comprises at least one compound A, a liquid or solid carrier and, if appropriate, at least one surfactant and/or at least one customary auxiliary, and a second component which in turn comprises at least one compound B, a liquid or solid carrier and, if appropriate, at least one surfactant and/or at least one customary auxiliary. More details, e.g. as to suitable liquid and solid carriers, surfactants and customary auxiliaries are described below.

The “combined” use of at least one pyrazole compound A with and at least one compound B or the treatment according to the invention with the at least one pyrazole compound I “in combination with” at least one compound B on the one hand can be understood as using a physical mixture of at least one pyrazole compound A and at least one compound B. On the other hand, the combined use may also consist in using the at least one pyrazole compound A and the at least one compound B separately, but within a sufficiently short time of one another so that the desired effect can take place. More detailed illustrations of the combined use can be found in the specifications below.

The term “invertebrate pest” (also referred to as animal pests) as used herein encompasses animal populations, such as insects, arachnids and nematodes, which may attack plants, thereby causing substantial damage to the plants attacked, as well as ectoparasites which may infest animals, in particular warm blooded animals such as e.g. mammals or birds, or other higher animals such as reptiles, amphibians or fish, thereby causing substantial damage to the animals infested.

The term “compound(s) according to the invention”, or “compound(s) of formula I” or “pyrazole compound(s) A” comprises the compound(s) as defined herein as well as a stereoisomer, salt, tautomer or N-oxide thereof. The term “compound(s) of the present invention” is to be understood as equivalent to the term “compound(s) according to the invention”, therefore also comprising a stereoisomer, salt, tautomer or N-oxide thereof.

The term “stereoisomers” encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).

Depending on the substitution pattern, the compounds of formula I may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers. One center of chirality is the carbon atom carrying radicals R³, R⁴ and R⁵. The invention provides both the pure enantiomers or diastereomers and their mixtures and the use according to the invention of the pure enantiomers or diastereomers of the compound I or its mixtures. Suitable compounds of the formula I also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof.

The term “N-oxide” relates to a form of compounds I in which at least one nitrogen atom is present in oxidized form (as NO).

The compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have a different macroscopic properties such as stability or show different biological properties such as activities. The present invention includes both amorphous and crystalline compounds of the formula I, mixtures of different crystalline states of the respective compound I, as well as amorphous or crystalline salts thereof.

Salts of the compounds of the formula I are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid of the anion in question if the compound of formula I has a basic functionality or by reacting an acidic compound of formula I with a suitable base.

Suitable agriculturally acceptable salts are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention. Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH⁴) and substituted ammonium in which one to four of the hydrogen atoms are replaced by C₁-C₄-alkyl, C₁-C₄-hydroxyalkyl, C₁-C₄-alkoxy, C₁-C₄-alkoxy-C₁-C₄-alkyl, hydroxy-C₁-C₄-alkoxy-C₁-C₄-alkyl, phenyl or benzyl. Examples of substituted ammonium ions comprise methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2-(2-hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzl-triethyl-ammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C₁-C₄-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C₁-C₄-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C₁-C₄-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting a compound of formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

By the term “veterinarily acceptable salts” is meant salts of those cations or anions which are known and accepted in the art for the formation of salts for veterinary use. Suitable acid addition salts, e.g. formed by compounds of formula I containing a basic nitrogen atom, e.g. an amino group, include salts with inorganic acids, for example hydrochlorides, sulphates, phosphates, and nitrates and salts of organic acids for example acetic acid, maleic acid, dimaleic acid, fumaric acid, difumaric acid, methane sulfenic acid, methane sulfonic acid, and succinic acid. The organic moieties mentioned in the above definitions of the variables are—like the term halogen—collective terms for individual listings of the individual group members. The prefix C_(n)-C_(m) indicates in each case the possible number of carbon atoms in the group.

The term “halogen” denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine, chlorine or bromine.

The term “alkyl” as used herein and in the alkyl moieties of alkylthio (also referred to as alkylsulfanyl), alkylsulfinyl, and alkylsulfonyl denotes in each case a straight-chain or branched alkyl group having usually from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms and in particular from 1 to 3 carbon atoms. Examples of an alkyl group are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, iso-butyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl.

The term “alkenyl” as used herein denotes in each case a singly unsaturated hydrocarbon radical having usually 2 to 6, preferably 2 to 4 carbon atoms, e.g. vinyl, allyl(2-propen-1-yl), 1-propen-1-yl, 2-propen-2-yl, methallyl(2-methylprop-2-en-1-yl), 2-buten-1-yl, 3-buten-1-yl, 2-penten-1-yl, 3-penten-1-yl, 4-penten-1-yl, 1-methylbut-2-en-1-yl, 2-ethylprop-2-en-1-yl and the like.

The term “alkynyl” as used herein denotes in each case a singly unsaturated hydrocarbon radical having usually 2 to 6, preferably 2 to 4 carbon atoms, e.g. ethynyl, propargyl (2-propyn-1-yl), 1-propyn-1-yl, 1-methylprop-2-yn-1-yl), 2-butyn-1-yl, 3-butyn-1-yl, 1-pentyn-1-yl, 3-pentyn-1-yl, 4-pentyn-1-yl, 1-methylbut-2-yn-1-yl, 1-ethylprop-2-yn-1-yl and the like.

The term “haloalkyl” as used herein and in the haloalkyl moieties of haloalkoxy, haloalkylthio, haloalkylsulfonyl and haloalkylsulfinyl, denotes in each case a straight-chain or branched alkyl group having usually from 1 to 6 carbon atoms, frequently from 1 to 4 carbon atoms, wherein the hydrogen atoms of this group are partially or totally replaced with halogen atoms. Preferred haloalkyl moieties are selected from C₁-C₂-haloalkyl, in particular from C₁-C₂-fluoroalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, and the like.

The term “alkoxy” as used herein denotes in each case a straight-chain or branched alkyl group which is bound via an oxygen atom and has usually from 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms. Examples of an alkoxy group are methoxy, ethoxy, n-propoxy, isopropoxy, n-butyloxy, 2-butyloxy, iso-butyloxy, tert.-butyloxy, and the like.

The term “alkoxyalkyl” as used herein refers to alkyl usually comprising 1 to 2 carbon atoms, wherein 1 carbon atom carries an alkoxy radical usually comprising 1 or 2 carbon atoms as defined above. Examples are CH₂OCH₃, CH₂—OC₂H₅, 2-(methoxy)ethyl, and 2-(ethoxy)ethyl.

The term “alkylcarbonyl” is a C₁-C₂-alkyl (“C₁-C₂-alkoxycarbonyl”) group, as defined above, attached via a carbonyl [C(═O)] group. Examples are methylcarbonyl and ethylcarbonyl.

The term “alkoxycarbonyl” is a C₁-C₂-alkoxy (“C₁-C₂-alkoxycarbonyl”) group, as defined above, attached via a carbonyl [C(═O)] group. Examples are methoxycarbonyl and ethoxycarbonyl.

The term “alkylidene” as used herein refers to a divalent group derived from an alkane usually comprising 1 to 2 carbon atoms, wherein two hydrogen atoms are removed from the same carbon atom, the free valencies being part of a double bond. Examples are methylidene (═CH₂) and ethylidene (═CH(CH₃)).

The term “cycloalkyl” as used herein and in the cycloalkyl moieties of cycloalkoxy and cyclo-alkylmethyl denotes in each case a monocyclic cycloaliphatic radical having usually from 3 to 6 carbon atom. Examples are cyclopropyl (c-C₃H₅), cyclobutyl (c-C₄H₇), cyclopentyl (c-C₅H₉), and cyclohexyl (c-C₆H₁₁).

The term “cycloalkenyl” as used herein denotes in each case a monocyclic monounsaturated hydrocarbon groups having 5 or 6 carbon ring members. Examples are cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl and cyclohexen-4-yl.

The term “heterocyclyl” includes in general 3- to 6-membered, in particular 5- or 6-membered monocyclic heterocyclic non-aromatic radicals. The heterocyclic non-aromatic radicals usually comprise 1 or 2 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO₂.

Examples of 5-, or 6-membered heterocyclic radicals comprise saturated or unsaturated, non-aromatic heterocyclic rings, such as oxiranyl, oxetanyl, thietanyl, thietanyl-S-oxid (S-oxothietanyl), thietanyl-S-dioxid (S-dioxothiethanyl), pyrrolidinyl, pyrrolinyl, pyrazolinyl, tetrahy-drofuranyl, dihydrofuranyl, 1,3-dioxolanyl, thiolanyl, S-oxothiolanyl, S-dioxothiolanyl, dihydrothienyl, S-oxodihydrothienyl, S-dioxodihydrothienyl, oxazolidinyl, oxazolinyl, thiazolinyl, oxathiolanyl, piperidinyl, piperazinyl, pyranyl, dihydropyranyl, tetrahydropyranyl, 1,3- and 1,4-dioxanyl, thiopyranyl, S.oxothiopyranyl, S-dioxothiopyranyl, dihydrothiopyranyl, S-oxodihydrothiopyranyl, S-dioxodihydrothiopyranyl, tetrahydrothiopyranyl, S-oxotetrahydrothiopyranyl, S-dioxotetrahydrothiopyranyl, morpholinyl, thiomorpholinyl, 5-oxothiomorpholinyl, 5-dioxothiomorpholinyl, thiazinyl and the like.

The term “monospiro 5- to 10-membered carbocycle” refers to a bicyclic ring system of 5-, 6-, 7-, 8-, 9- or 10 carbon atoms having one atom in common (spiroatom). Examples are spiro[2.2]pentyl, spiro[2.3]hexyl, spiro[2.4]heptyl, spiro[3.4]octyl, spiro[3.5]nonyl, spiro[3.6]deyl, spiro[4.4]nonyl and spiro[4.5]decyl.

The term “dispiro 5- to 10-membered carbocycle” refers to a tricyclic ring system of 5-, 6-, 7-, 8-, 9- or 10 carbon atoms having 2 spiroatoms. Examples are dispiro[2.0.2.1]heptyl, dispiro[2.0.3.1]octyl, dispiro[3.0.3.1]nonyl, dispiro[2.0.4.1]nonyl, dispiro[2.1.2.1]octyl, dispiro[2.1.3.1]nonyl and dispiro[3.1.3.1]decyl.

The term “monospiro or dispiro 5- to 10-membered heterocycle” refers to a bicyclic or tricyclic ring system of 5-, 6-, 7-, 8-, 9- or 10 ring atoms which has one or two spiroatoms. The heterocyclic ring system usually comprise 1 or 2 heteroatoms selected from N, O and S as ring members, where S-atoms as ring members may be present as S, SO or SO₂. Examples are:

In the above structures # denotes the attachment point to the remainder of the molecule. The attachment point is not restricted to the ring on which is shown, but can be on either of the spiro rings, and may be on a carbon or on a nitrogen ring atom. If the rings carry one or more substituents, these may be bound to carbon and/or to nitrogen ring atoms.

The commercially available further compound B may be found in The Pesticide Manual, 13th Edition, British Crop Protection Council (2003) among other publications.

The phthalamide A11.1 is known from WO 2007/101540. The isoxazoline compounds A12.1 to A12.8 have been described in e.g. WO2005/085216, WO 2007/079162, WO 2007/026965, WO 2009/126668 and WO2009/051956. The anthranilamides A13.1 to A13.6 have been described in WO 2008/72743 and WO 200872783, those A13.7 to A13.12 in WO 2007/043677. Malononitrile compounds as those (A14.1) and (A14.2) have been described in WO 02/089579, WO 02/090320, WO 02/090321, WO 04/006677, WO 05/068423, WO 05/068432 and WO 05/063694. The aminofuranone compounds A16.1 to A16.7 have been described eg. in WO 2007/115644. The alkynylether compound A17.1 is described e.g. in JP 2006131529. Organic sulfur compounds have been described in WO 2007060839. The pyripyropene derivative afidopyropen has been described in WO 2008/66153 and WO 2008/108491. The pyridazin compound A17.2 has been described in JP 2008/115155.

The active compounds B mentioned above of groups F.1 to F.11, their preparation and their action against harmful fungi are generally known (cf., for example, http://www.hclrss.demon.co.uk/index.html); they are commercially available.

Benalaxyl, methyl N-(phenylacetyl)-N-(2,6-xylyl)-DL-alaninate (DE 29 03 612); metalaxyl, methyl N-(methoxyacetyl)-N-(2,6-xylyl)-DL-alaninate (GB 15 00 581); ofurace, (RS)-α-(2-chloro-N-2,6-xylylacetamido)-γ-butyrolactone [CAS RN 58810-48-3]; oxadixyl; N-(2,6-dimethylphenyl)-2-methoxy-N-(2-oxo-3-oxazolidinyl)acetamide (GB 20 58 059); aldimorph, “4-alkyl-2,5(or 2,6)-dimethylmorpholine”, comprising 65-75% of 2,6-dimethylmorpholine and 25-35% of 2,5-dimethylmorpholine, comprising more than 85% of 4-dodecyl-2,5(or 2,6)-dimethylmorpholine, where “alkyl” also includes octyl, decyl, tetradecyl and hexadecyl, with a cis/trans ratio of 1:1 [CAS RN 91315-15-0]; dodine, 1-dodecylguanidinium acetate (Plant Dis. Rep., Vol. 41, p. 1029 (1957)); dodemorph, 4-cyclododecyl-2,6-dimethylmorpholine (DE-A 11 98125); fenpropimorph, (RS)-cis-4-[3-(4-tertbutylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine (DE-A 27 52 096); fenpropidin, (RS)-1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine (DE-A 27 52 096); guazatine, mixture of the reaction products from the amidation of technical grade iminodi(octamethylene)diamine, comprising various guanidines and polyamines [CAS RN 108173-90-6]; iminoctadine, 1,1′-iminodi(octamethylene)diguanidine (Congr. Plant Pathol., 1., p. 27 (1968); spiroxamine, (8-tert-butyl-1,4-dioxaspiro[4.5]dec-2-yl)diethylamine (EP-A 281 842); tridemorph, 2,6-dimethyl-4-tridecylmorpholine (DE-A 11 64 152); pyrimethanil, 4,6-dimethylpyrimidin-2-ylphenylamine (DD-A 151 404); mepanipyrim, (4-methyl-6-prop-1-ynylpyrimidin-2-yl)phenylamine (EP-A 224 339); cyprodinil, (4-cyclopropyl-6-methylpyrimidin-2-yl)phenylamine (EP-A 310 550); cycloheximide, 4-{(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl}piperidine-2,6-dione [CAS RN 66-81-9]; griseofulvin, 7-chloro-2′,4,6-trimethoxy-6′-methylspiro[benzofuran-2(3H)-1′-cyclohex-2′-ene]-3,4′-dione [CAS RN 126-07-8]; kasugamycin, 3-O-[2-amino-4-[(carboxyiminomethyl)amino]-2,3,4,6-tetradeoxy-α-D-arabino-hexopyranosyl)-D-chiro-inositol [CAS RN 6980-18-3]; natamycin, (8E,14E,16E,18E,20E)-(1R,3S,5R,7R,12R,22R,24S,25R,26S)-22-(3-amino-3,6-dideoxy-β-D-mamopyranosyloxy)-1,3,26-trihydroxy-12-methyl-10-oxo-6,11,28-trioxatricyclo[22.3.1.0^(5,7)]octacosa-8,14,16,18,20-pentaene-25-carboxylic acid [CAS RN 7681-93-8]; polyoxin, 5-(2-amino-5-O-carbamoyl-2-deoxy-L-xylonannido)-1-(5-carboxy-1,2,3,4-tetrahydro-2,4-dioxopyrimidin-1-yl)-1,5-dideoxy-β-D-allofuranuronic acid [CAS RN 22976-86-9]; streptomycin, 1,1′-{1-L-(1,3,5/2,4,6)-4-[5-deoxy-2-O-(2-deoxy-2-methylamino-α-L-glucopyranosyl)-3-C-formyl-α-L-Iyxofuranosyloxy]-2,5,6-trihydroxycyclohex-1,3-ylene}diguanidine (J. Am. Chem. Soc. Vol. 69, p. 1234 (1947)); bitertanol, β-([1,1′-biphenyl]-4-yloxy)-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol (DE-A 23 24 020); bromuconazole, 1-[[4-bromo-2-(2,4-dichlorophenyl)tetrahydro-2-furanyl]methyl]-1H-1,2,4-triazole (Proc. 1990 Br. Crop. Prot. Conf. Pests Dis. Vol. 1, p. 459); cyproconazole, 2-(4-chlorophenyl)-3-cyclopropyl-1-[1,2,4]triazol-1-ylbutan-2-ol (U.S. Pat. No. 4,664,696); difenoconazole, 1-{2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-[1,3]dioxolan-2-ylmethyl}-1H-[1,2,4]triazole (GB-A2 098 607); diniconazole, (βE)-β-[(2,4-dichlorophenyl)methylene]-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol (Noyaku Kagaku, 1983, Vol. 8, p. 575); enilconazole (imazalil), 1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy)ethyl]-1H-imidazole (Fruits, 1973, Vol. 28, p. 545); epoxiconazole, (2RS,3SA)-1-[3-(2-chlorophenyl)-2,3-epoxy-2-(4-fluorophenyl)propyl]-1H-1,2,4-triazole (EP-A 196 038); fenbuconazole, α-[2-(4-chlorophenyl)ethyl]-α-phenyl-1H-1,2,4-triazole-1-propanenitrile (Proc. 1988 Br. Crop Prot. Conf. Pests Dis., Vol. 1, p. 33); fluquinconazole, 3-(2,4-dichlorophenyl)-6-fluoro-2-[1,2,4]triazol-1-yl-3H-quinazolin-4-one (Proc. Br. Crop Prot. Conf.—Pests Dis., 5-3, 411 (1992)); flusilazole, 1-{[bis(4-fluorophenyl)methylsilanyl]methyl}-1H-[1,2,4]triazole (Proc. Br. Crop Prot. Conf.—Pests Dis., Vol. 1, p. 413 (1984)); flutriafol, α-(2-fluorophenyl)-α-(4-fluorophenyl)-1H-1,2,4-triazole-1-ethanol (EP-A 15756); hexaconazole, 2-(2,4-dichlorophenyl)-1-[1,2,4]triazol-1-ylhexan-2-ol (CAS RN 79983-71-4); ipconazole, 2-[(4-chlorophenyl)methyl]-5-(1-methylethyl)-1-(1H-1,2,4-triazol-1-yl-methyl)cyclopentanol (EP-A 267 778); metconazole, 5-(4-chlorobenzyl)-2,2-dimethyl-1-[1,2,4]triazol-1-ylmethylcyclopentanol (GB 857 383); myclobutanil, 2-(4-chlorophenyl)-2-[1,2,4]triazol-1-ylmethylpentanenitrile (CAS RN 88671 89 0); penconazole, 1-[2-(2,4-dichloro-phenyl)pentyl]-1H-[1,2,4]triazole (Pesticide Manual, 12th Ed. 2000, p. 712); propiconazole, 1-[[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole (BE 835 579); prochloraz, N-(propyl-[2-(2,4,6-trichlorophenoxy)ethyl])imidazole-1-carboxamide (U.S. Pat. No. 3,991,071); prothioconazole, 2-[2-(1-chlorocyclopropyl)-3-(2-chlorophenyl)-2-hydroxypropyl]-2,4-dihydro[1,2,4]triazole-3-thione (WO 96/16048); simeconazole, α-(4-fluorophenyl)-α-[(trimethylsilyl)methyl]-1H-1,2,4-triazole-1-ethanol [CAS RN 149508-90-7], tebuconazole, 1-(4-chlorophenyl)-4,4-dimethyl-3-[1,2,4]triazol-1-ylmethylpentan-3-ol (EP-A 40 345); tetraconazole, 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoroethoxy)propyl]-1H-1,2,4-triazole (EP-A 234 242); triadimefon, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone (BE 793 867); triadimenol, β-(4-chlorophenoxy)-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol (DE-A 3 24 010); triflumizol, (4-chloro-2-trifluoromethylphenyl)-(2-propoxy-1-[1,2,4]triazol-1-ylethylidene)-amine (JP-A 79/119 462); triticonazole, (5E)-5-[(4-chlorophenyl)methylene]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (FR 26 41 277); iprodione, N-isopropyl-3-(3,5-dichlorophenyl)-2,4-dioxoimidazolidine-1-carboxamide (GB 13 12 536); myclozolin, (RS)-3-(3,5-dichlorophenyl)-5-methoxymethyl-5-methyl-1,3-oxazolidine-2,4-dione [CAS RN 54864-61-8]; procymidone, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide (U.S. Pat. No. 3,903,090); vinclozolin, 3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione (DE-A 22 07 576); ferbam, iron(3+) dimethyldithiocarbamate (U.S. Pat. No. 1,972,961); nabam, disodium ethylenebis(dithiocarbamate) (U.S. Pat. No. 2,317,765); maneb, manganese ethylenebis(dithiocarbamate) (U.S. Pat. No. 2,504,404); mancozeb, manganese ethylenebis(dithiocarbamate) polymer complex zinc salt (GB 996 264); metam, methyldithiocarbaminic acid (U.S. Pat. No. 2,791,605); metiram, zinc ammoniate ethylenebis(dithiocarbamate) (U.S. Pat. No. 3,248,400); propineb, zinc propylenebis(dithiocarbamate) polymer (BE 611 960); polycarbamate, bis(dimethylcarbamodithioato-κ S,κ S′)[p-[[1,2-ethanediylbis[carbamodithioato-κ S,κ S′]](2-)]]di[zinc] [CAS RN 64440-88-6]; thiram, bis(dimethylthiocarbamoyl)disulfide (DE-A 642 532); ziram, dimethyldithiocarbamate [CAS RN 137-30-4]; zineb, zinc ethylenebis(dithiocarbamate) (U.S. Pat. No. 2,457,674); anilazine, 4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazine-2-amine (U.S. Pat. No. 2,720,480); benomyl, N-butyl-2-acetylaminobenzimidazole-1-carboxamide (U.S. Pat. No. 3,631,176); boscalid, 2-chloro-N-(4′-chlorobiphenyl-2-yl)nicotinamide (EP-A 545 099); carbendazim, methyl(1H-benzimidazol-2-yl)carbamate (U.S. Pat. No. 3,657,443); carboxin, 5,6-dihydro-2-methyl-N-phenyl-1,4-oxathiine-3-carboxamide (U.S. Pat. No. 3,249,499); oxycarboxin, 5,6-dihydro-2-methyl-1,4-oxathiine-3-carboxanilide 4,4-dioxide (U.S. Pat. No. 3,399,214); cyazofamid, 4-chloro-2-cyano-N,N-dimethyl-5-(4-methylphenyl)-1H-imidazole-1-sulfonamide (CAS RN 120116-88-3]; dazomet, 3,5-dimethyl-1,3,5-thiadiazinane-2-thione (Bull. Soc. Chinn. Fr. Vol. 15, p. 891 (1897)); diflufenzopyr, 2-{1-[4-(3,5-difluorophenyl)semicarbazono]ethyl}nicotinic acid [CAS RN 109293-97-2]; dithianon, 5,10-dioxo-5,10-dihydronaphtho[2,3-b][1,4]dithiin-2,3-dicarbonitrile (GB 857 383); famoxadone, (RS)-3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione [CAS RN 131807-57-3]; fenamidone, (S)-1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one [CAS RN 161326-34-7]; fenarimol, α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol (GB 12 18 623); fuberidazole, 2-(2-furanyl)-1H-benzimidazole (DE-A 12 09 799); flutolanil, α,α,α-trifluoro-3′-isopropoxy-o-toluanilide (JP 1104514); furametpyr, 5-chloro-N-(1,3-dihydro-1,1,3-trimethyl-4-isobenzofuranyl)-1,3-dimethyl-1H-pyrazole-4-carboxamide [CAS RN 123572-88-3]; isoprothiolane, diisopropyl 1,3-dithiolan-2-ylidenemalonate (Proc. Insectic. Fungic. Conf. 8. Vol. 2, p. 715 (1975)); mepronil, 3′-isopropoxy-o-toluanilide (U.S. Pat. No. 3,937,840); nuarimol, α-(2-chlorophenyl)-α-(4-fluorophenyl)-5-pyrimidinemethanol (GB 12 18 623); fluopicolide (picobenzamid), 2,6-dichloro-N-(3-chloro-5-trifluoromethylpyridin-2-ylmethyl)benzamide (WO 99/42447); probenazole, 3-allyloxy-1,2-benzothiazole 1,1-dioxide (Agric. Biol. Chem. Vol. 37, p. 737 (1973)); proquinazid, 6-iodo-2-propoxy-3-propylquinazolin-4(3H)-one (WO 97/48684); pyrifenox, 2′,4′-dichloro-2-(3-pyridyl)acetophenone (EZ)-O-methyloxime (EP 49 854); pyroquilon, 1,2,5,6-tetrahydropyrrolo[3,2,1-ij]quinolin-4-one (GB 139 43 373); quinoxyfen, 5,7-dichloro-4-(4-fluorophenoxy)quinoline (U.S. Pat. No. 5,240,940); silthiofam, N-allyl-4,5-dimethyl-2-(trimethylsilyl)thiophene-3-carboxamide [CAS RN 175217-20-6]; thiabendazole, 2-(1,3-thiazol-4-yl)benzimidazole (U.S. Pat. No. 3,017,415); thifluzamide, 2′,6′-dibromo-2-methyl-4′-trifluoromethoxy-4-trifluoromethyl-1,3-thiazole-5-carboxanilide [CAS RN 130000-40-7]; thiophanate-methyl, 1,2-phenylenebis(iminocarbonothioyl)bis(dimethylcarbamate) (DE-A 19 30 540); tiadinil, 3′-chloro-4,4′-dimethyl-1,2,3-thiadiazole-5-carboxanilide [CAS RN 223580-51-6]; tricyclazole, 5-methyl-1,2,4-triazolo[3,4-b][1,3]benzothiazole [CAS RN 41814-78-2]; triforine, N,N-{piperazine-1,4-diylbis[(trichloromethyl)methylene]}diformamide (DE-A 19 01 421); 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine (WO 98/46607) and other triazolo pyrimidine (EP-A 71 792; EP-A 141 317; WO 03/009687; WO 05/087771; WO 05/087772; WO 05/087773; WO 2006/087325; WO 2006/092428); Bordeaux mixture, mixture of CuSO₄×3Cu(OH)₂×3CaSa₄ [CAS RN 8011-63-0]; copper acetate, Cu(OCOCH₃)₂ [CAS RN 8011-63-0]; copper oxychloride, Cu₂Cl(OH)₃ [CAS RN 1332-40-7]; basic copper sulfate, CuSO₄ [CAS RN 1344-73-6]; binapacryl, (RS)-2-sec-butyl-4,6-dinitrophenyl 3-methylcrotonate [CAS RN 485-31-4]; dinocap, mixture of 2,6-dinitro-4-octylphenylcrotonate and 2,4-dinitro-6-octylphenylcrotonate, where “octyl” is a mixture of 1-methylheptyl, 1-ethylhexyl and 1-propylpentyl (U.S. Pat. No. 2,526,660); dinobuton, (RS)-2-sec-butyl-4,6-dinitrophenyl isopropyl carbonate [CAS RN 973-21-7]; nitrothal-isopropyl, diisopropyl 5-nitroisophthalate (Proc. Br. Insectic. Fungic. Conf. 7., Vol. 2, p. 673 (1973)); fenpiclonil, 4-(2,3-dichlorophenyl)-1H-pyrrole-3-carbonitrile (Proc. 1988 Br. Crop Prot. Conf. Pests Dis., Vol. 1, p. 65); fludioxonil, 4-(2,2-difluorobenzo[1,3]dioxol-4-yl)-1H-pyrrole-3-carbonitrile (The Pesticide Manual, publ. The British Crop Protection Council, 10th ed. 1995, p. 482); acibenzolar-S-methyl, methyl 1,2,3-benzo-thiadiazole-7-carbothioate [CAS RN 135158-54-2]; flubenthiavalicarb (benthiavalicarb), isopropyl {(S)-1-[(1R)-1-(6-fluorobenzothiazol-2-yl)-ethylcarbamoyl]-2-methylpropyl}carbamate (JP-A 09/323 984); carpropamid, 2,2-dichloro-N-[1-(4-chlorophenyl)ethyl]-1-ethyl-3-methyl-cyclopropanecarboxamide [CAS RN 104030-54-8]; chlorothalonil, 2,4,5,6-tetrachloro-isophthalonitrile (U.S. Pat. No. 3,290,353); cyflufenamid, (Z)-N-[α-(cyclopropylmethoxyimino)-2,3-difluoro-6-(trifluoromethyl)benzyl]-2-phenylacetamide (WO 96/19442); cymoxanil, 1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea (U.S. Pat. No. 3,957,847); diclomezine, 6-(3,5-dichlorophenyl-p-tolyl)pyridazin-3(2H)-one (U.S. Pat. No. 4,052,395;) diclocymet, (RS)-2-cyano-N-[(R)-1-(2,4-dichlorophenyl)ethyl]-3,3-dimethylbutyramide [CAS RN 139920-32-4]; diethofencarb, isopropyl 3,4-diethoxycarbanilate (EP-A 78 663); edifenphos, O-ethyl S,S-diphenyl phosphorodithioate (DE-A 14 93 736); ethaboxam, N-(cyano-2-thienylmethyl)-4-ethyl-2-(ethylamino)-5-thiazolecarboxamide (EP-A 639 574); fenhexamid, N-(2,3-dichloro-4-hydroxyphenyl)-1-methylcyclohexanecarboxamide (Proc. Br. Crop Prot. Conf.—Pests Dis., 1998, Vol. 2, p. 327); fentin-acetate, triphenyltin (U.S. Pat. No. 3,499,086); fenoxanil, N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propanamide (EP-A 262 393); ferimzone, (Z)-2′-methylacetophenone-4,6-dimethylpyrimidin-2-ylhydrazone [CAS RN 89269-64-7]; fluazinam, 3-chloro-N-[3-chloro-2,6-dinitro-4-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-2-pyridinamine (The Pesticide Manual, publ. The British Crop Protection Council, 10th ed. (1995), p. 474); fosetyl, fosetyl-aluminum, ethylphosphonate (FR 22 54 276); iprovalicarb, isopropyl [(1S)-2-methyl-1-(1-p-tolylethylcarbamoyl)propyl]carbamate (EP-A 472 996); hexachlorobenzene (C. R. Seances Acad. Agric. Fr., Vol. 31, p. 24 (1945)); mandipropamid, (RS)-2-(4-chlorophenyl)-N-[3-methoxy-4-(prop-2-ynyloxy)phenethyl]-2-(prop-2-ynyloxy)acetamide (WO 03/042166); metrafenone, 3′-bromo-2,3,4,6′-tetramethoxy-2′,6-dimethylbenzophenone (U.S. Pat. No. 5,945,567); pencycuron, 1-(4-chlorobenzyl)-1-cyclopentyl-3-phenylurea (DE-A 27 32 257); penthiopyrad, (RS)-N-[2-(1,3-dimethylbutyl)-3-thienyl]-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide (JP 10/130268); propamocarb, isopropyl 3-(dimethylamino)propylcarbamate (DE-A 15 67 169); phthalide (DE-A 16 43 347); toloclofos-methyl, 0-2,6-dichloro-p-tolyl 0,0-dimethyl phosphorothioate (GB 14 67 561); quintozene, pentachloronitrobenzene (DE-A 682 048); zoxamide, (RS)-3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-p-toluamide [CAS RN 156052-68-5]; captafol, N-(1,1,2,2-tetrachloroethylthio)cyclohex-4-ene-1,2-dicarboximide (Phytopathology, Vol. 52, p. 754 (1962)); captan, N-(trichloromethylthio)cyclohex-4-ene-1,2-dicarboximide (U.S. Pat. No. 2,553,770); dichlofluanid, N-dichlorofluoromethylthio-N,N-dimethyl-N-phenylsulfamide (DE-A 11 93 498); folpet, N-(trichloromethylthio)phthalimide (U.S. Pat. No. 2,553,770); tolylfluanid, N-dichlorofluoro-methylthio-N,N-dimethyl-N-p-tolylsulfamide (DE-A 11 93 498); dimethomorph, 3-(4-chloro-phenyl)-3-(3,4-dimethoxyphenyl)-1-morpholin-4-yl-propenone (EP-A 120 321); flumetover, 2-(3,4-dimethoxyphenyl)-N-ethyl-α,α,α-trifluoro-N-methyl-p-toluamide [AGROW no. 243, 22 (1995)]; flumorph, 3-(4-fluorophenyl)-3-(3,4-dimethoxyphenyl)-1-morpholin-4-ylpropenone (EP-A 860 438); N-(4′-bromobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-trifluoromethylbiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide, N-(4′-chloro-3′-fluorobiphenyl-2-yl)-4-difluoromethyl-2-methylthiazole-5-carboxamide (WO 03/66610); N-(3′,4′-dichloro-4-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide and N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-difluoromethyl-1-methylpyrazole-4-carboxamide (WO 03/70705); N-(2-cyanophenyl)-3,4-dichloroisothiazole-5-carboxamide (WO 99/24413); N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl)ethyl)-2-methanesulfonylamino-3-methylbutyramide, N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenypethyl)-2-ethanesulfonylamino-3-methylbutyramide (WO 04/49804); N-(2-bicycloprop-2-ylphenyl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide is a mixture of the diastereomers N-(trans-2-bicycloprop-2-ylphenyl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide and N-(cis-2-bicycloprop-2-ylphenyl)-3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxamide (WO 03/074491 and WO 06/015866); 3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine (EP-A 10 35 122); 2-butoxy-6-iodo-3-propylchromen-4-one (WO 03/14103); N,N-dimethyl-3-(3-bromo-6-fluoro-2-methylindole-1-sulfonyl)[1,2,4]triazole-1-sulfonamide (EP-A 10 31 571); methyl(2-chloro-5-[1-(3-methylbenzyloxyimino)ethyl]benzyl)carbamate, methyl(2-chloro-5-[1-(6-methylpyridin-2-ylmethoxyimino)ethyl]benzyl)carbamate (EP-A 12 01 648); methyl 3-(4-chloro-phenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)propionate (EP-A 10 28 125); azoxystrobin, methyl 2-{2-[6-(2-cyano-1-vinylpenta-1,3-dienyloxy)pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate (EP-A 382 375), dimoxystrobin, (E)-2-(methoxyimino)-N-methyl-2-[α-(2,5-xylyloxy)-o-tolyl]acetamide (EP-A 477 631); fluoxastrobin, (E)-{2-[6-(2-chlorophenoxy)-5-fluoropyrimidin-4-yloxy]phenyl}(5,6-dihydro-1,4,2-dioxazin-3-yl)methanone 0-methyloxime (WO 97/27189); kresoxim-methyl, methyl (E)-methoxyimino[α-(o-tolyloxy)-o-tolyl]acetate (EP-A 253 213); metominostrobin, (E)-2-(methoxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamide (EP-A 398 692); orysastrobin, (2E)-2-(methoxyimino)-2-{2-[(3E,5E,6E)-5-(methoxyimino)-4,6-dimethyl-2,8-dioxa-3,7-diazanona-3,6-dien-1-yl]phenyl}-N-methylacetamide (WO 97/15552); picoxystrobin, methyl 3-methoxy-2-[2-(6-trifluoromethylpyridin-2-yloxymethyl)phenyl]acrylate (EP-A 278 595); pyraclostrobin, methyl N-{2-[1-(4-chlorophenyl)-1H-pyrazol-3-yloxymethyl]phenyl}(N-methoxy)carbamate (WO 96/01256); trifloxystrobin, methyl(E)-methoxyimino-{(E)-α-[1-(α,α,α-trifluoro-m-tolyl)ethylideneaminooxy]-o-tolyl}acetate (EP-A 460 575); methyl 2-[ortho-(2,5-dimethylphenyloxymethylene)phenyl]-3-methoxyacrylate (EP-A 226 917); 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine (WO 98/46608); 3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide (WO 99/24413), compounds of the formula III (WO 04/049804); N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl)ethyl)-2-methanesulfonylamino-3-methylbutyramide and N-(2-(4-[3-(4-chlorophenyl)prop-2-ynyloxy]-3-methoxyphenyl)ethyl)-2-ethanesulfonylamino-3-methylbutyramide (WO 03/66609); 2-butoxy-6-iodo-3-propylchromen-4-one (WO 03/14103); N,N-dimethyl-3-(3-bromo-6-fluoro-2-methylindole-1-sulfonyl)-[1,2,4]triazole-1-sulfonamide (WO 03/053145); methyl 3-(4-chlorophenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino)-propanoate (EP-A 1028125).

We have accordingly found that several objects can be achieved by the mixtures, defined at the outset, of the active compounds of formula I and compound B. Moreover, we have found that simultaneous, that is joint or separate, application of at least one compound I and at least one of the active compounds B or successive application of at least one of the compound(s) of formula I and at least one of the active compounds B allows better control of animal pests and/or harmful fungi than is possible with the individual compounds alone (synergistic mixtures).

The compounds of formula I can be used as synergists for a large number of different fungicidal active compounds. By simultaneous, that is joint or separate, application of compound(s) of formula I with at least one active compound B, the fungicidal and/or insecticidal activity, resp., is increased in a superadditive manner.

The compounds of the formula I can be present in different crystal modifications, which may differ in biological activity.

The remarks made below as to preferred embodiments of the variables (substituents) of the compounds of formula I are valid on their own as well as preferably in combination with each other, as well as in combination with the stereoisomers, salts, tautomers or N-oxides thereof.

The remarks made below concerning preferred embodiments of the variables further are valid on their own as well as preferably in combination with each other concerning the compounds of formula I, where applicable, as well as concerning the uses and methods according to the invention and the mixtures according to the invention.

In one embodiment of the invention the compounds of formula I have the following meanings:

-   R¹ is H, C₁-C₂-alkyl, or C₁-C₂-alkoxy-C₁-C₂-alkyl; -   R² is CH₃, CH₂F, CHF₂, or CF₃; -   R³ is C2-C6-alkyl, a radical R^(3a), or a radical R^(3b); -   R⁴ is C₁-C₄-alkyl, or a group mentioned for R^(3a); -   R⁵ is H, halogen, or a group mentioned for R⁴; -   R³ and R⁴ together with the carbon atom, to which they are attached,     may form a monocyclic three- to six-membered carbo- or heterocycle,     which may contain 1 or 2 heteroatom moieties selected from N—R^(c),     O, and S(O)_(k), with k being 0, 1 or 2, which carbo- or heterocycle     is unsubstituted or may be substituted by 1, 2, 3 or 4 radicals     R^(a3); -   R³ and R⁴ together with the carbon atom, to which they are attached,     may also form a monospiro or dispiro 5- to 10-membered carbo- or     heterocycle, which may contain 1 or 2 heteroatom moieties selected     from N—R^(c), O, and S(O)_(k), with k being 0, 1 or 2, which carbo-     or heterocycle is unsubstituted or may be substituted by 1, 2, 3 or     4 radicals R^(a3); -   R^(3a) is selected from the group consisting of CN, NO₂,     S(O)_(n)R^(b), C₁-C₄-haloalkyl, C₁-C₄-alkyl which is partially or     fully substituted by R^(a1), C₂-C₆-alkenyl, C₂-C₆-alkynyl,     C₁-C₆-alkoxy, wherein the C-atoms in the last 3 mentioned radicals     may be unsubstituted, or partially or fully substituted by R^(a2),     C₃-C₆-cycloalkyl and C₅-C₆-cycloalkenyl wherein the C-atoms in the     last 2 mentioned radicals may be unsubstituted, or partially or     fully substituted by R^(a3), -   R^(3b) is a monospiro or dispiro 5- to 10-membered carbo- or     heterocycle, which may contain 1 or 2 heteroatom moieties selected     from N—R^(c), O, and S(O)_(k), with k being 0 1 or 2, which     monospiro or dispiro 5 to 10-membered carbo- or heterocycle is     unsubstituted, or may be substituted by 1, 2, 3 or 4 radicals     R^(a3); -   R^(a1) is CN, NO₂, C(O)NH₂, C(S)NH₂, C₁-C₂-alkylcarbonyloxy,     C₁-C₄-alkoxy, C₁-C₂-haloalkoxy, C₁-C₂-alkyloxycarbonyl, or     S(O)_(n)R^(b); -   R^(a2) is halogen, or a group mentioned for R^(a1); -   R^(a3) is halogen, C₁-C₂-alkyl, C₁-C₂-alkoxy-C₁-C₂-alkyl,     C₁-C₂-alkyliden, or a group mentioned for R^(a1); -   n is 0, 1, or 2; -   R^(b) is selected from the group consisting of H, C₁-C₂-alkyl,     C₁-C₂-haloalkyl, C₃-C₆-cycloalkyl, and C₁-C₄-alkoxy, -   R^(c) is H, C₁-C₂-alkyl, C₁-C₂-haloalkyl, C₁-C₂-alkylcarbonyl, and     C₁-C₂-alkoxycarbonyl; the stereoisomers, salts, tautomers, and     N-oxides thereof.

Particularly suitable for the mixtures according to the invention are compounds of the formula I in which R¹ is H, C₁-C₂-alkyl, or C₁-C₂-alkoxymethyl. More preferably, R¹ is CH₃, or C₂H₅.

Particularly suitable for the mixtures according to the invention are compounds of the formula I in which R² is CH₃, CHF₂, or CF₃, especially CH₃.

Particularly suitable for the mixtures according to the invention are compounds of the formula I in which R³ is a radical R^(3b). In this context, R^(3b) is preferably a 5-, 6-, 7-, 8-, 9-, or 10-membered monospiro- or dispirocarbocycle which is unsubstituted or substituted by 1 or 2 radicals R^(a3). R^(a3), if present, is preferably selected from CN, C₁-C₂-haloalkyl, C₁-C₂-alkylidene, and C₁-C₂-alkoxy-C₁-C₂-alkyl. In another embodiment R^(a3) is haloalkyl, preferably CHF₂, or CF₃, preferred CF₃. Substituents R^(a3) are preferably in 1- or 4-position, if the carbocycle is monosubstituted and in 4,4-position, if the carbocycle is disubstituted. More preferably, R³ is spiro[2.2]pentyl, which is unsubstituted or carries one or two radicals R^(a3) or 7-dispiro[2.0.1.2]-heptyl which is unsubstituted or carries a radical R^(a3). R³ is even more preferably selected from the group consisting of spiro[2.2]pentyl, 2-methylene-spiro[2.2]pentyl, 1-CN-spiro[2.2]pentyl, 1-CF₃-spiro[2.2]pentyl, 4-CH₃-spiro[2.2]pentyl, 4,4-(CH₃)₂-spiro[2.2]pentyl, 4-(CH₂OCH₃)-spiro[2.2]pentyl, 4-CF₃-spiro[2.2]pentyl and 7-dispiro[2.0.2.1]-heptyl.

Particularly suitable for the mixtures according to the invention are compounds of the formula I in which R³ is selected from the group consisting of CN, C₂-C₆-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkyl which is substituted by one or two radicals R^(a1), or C₃-C₆-cycloalkyl, wherein the C-atoms of C₃-C₆-cycloalkyl are unsubstituted or substituted by 1 or 2 radicals R^(a3). In this context, R^(a1) is preferably selected from CN, C₁-C₂-alkoxy, C₁-C₂-alkylsulfanyl, C₁-C₂-haloalkoxy, and C₁-C₂-haloalkylsulfanyl. R^(a3) is preferably selected from CN, C₁-C₂-alkoxy, C₁-C₂-alkylsulfanyl, C₁-C₂-haloalkoxy, and C₁-C₂-haloalkylsulfanyl. One substituent R^(a3) is preferably in 1-position. More preferably, R³ is selected from CN, C₂-C₄-alkyl, C₁-C₄-fluoroalkyl, C₁-C₄-alkyl which is substituted by one or two radicals R^(a1), and C₃-C₆-cycloalkyl which is unsubstituted or carries one radical R^(a3). More preferably, R^(a1) is selected from CN, C₁-C₂-alkoxy, C₁-C₂-alkylsulfanyl, C₁-C₂-fluoroalkoxy, and C₁-C₂-fluoroalkoxysulfanyl. R^(a3) is preferably selected from CN, C₁-C₂-alkoxy, C₁-C₂-alkylsulfanyl, C₁-C₂-fluoroalkoxy, and C₁-C₂-fluoroalkylsulfanyl. Even more preferably, R³ is selected from CN, C₂-C₄-alkyl, C₁-C₄-haloalkyl, especially C₁-C₄-fluoroalkyl, C₁-C₂-alkoxy-C₁-C₄-alkyl, C₁-C₂-haloalkoxy-C₁-C₄-alkyl, especially C₁-C₂-fluoroalkoxy-C₁-C₄-alkyl, cyano-C₁-C₄-alkyl, C₁-C₂-alkylsulfanyl-C₁-C₄-alkyl, C₁-C₂-haloalkylsulfanyl-C₁-C₄-alkyl, especially C₁-C₂-fluoroalkylsulfanyl-C₁-C₄-alkyl, C₃-C₆-cycloalkyl, C₃-C₆-cycloalkyl which carries one radical R^(a3) selected from halogen, especially F, CN, C₁-C₂-alkyl, C₁-C₄-alkoxy, C₁-C₂-haloalkoxy, especially C₁-C₂-fluoroalkoxy, C₁-C₂-alkylsulfanyl and C₁-C₂-haloalkylsulfanyl, especially C₁-C₂-fluoroalkoxysulfanyl.

According to this embodiment, preferred examples for R³ are CN, C₂H₅, CH(CH₃)₂, CHF₂, CH₂F, CF₃, CH₂OCH₃, c-C₃H₅, 1-F-c-C₃H₄, 1-CN-c-C₃H₄, 1-CH₃-c-C₃H₄, 1-OCH₃-c-C₃H₄, 1-CF₃-c-C₃H₄, 1-OCF₃-c-C₃H₄, 1-SCH₃-c-C₃H₄, 1-SCF₃-c-C₃H₄, C(CH₃)₃, 1-F-1-methylethyl, 1-CN-1-methylethyl, 1-methoxy-1-methylethyl, 1-(trifluoromethoxy)-1-methylethyl, 1-(methylsulfanyl)-1-methylethyl, 1-(trifluoromethylsulfanyl)-1-methylethyl, 2,2,2-trifluoro-1,1-dimethylethyl, CHFCH₃, CH(CN)CH₃, CF₂CH₃, 1,1-dimethoxyethyl, 1-methoxyethyl, 1-(trifluoromethoxy)-ethyl, 1-(methylsulfanyl)ethyl, 1-(trifluoromethylsulfanyl)ethyl, 2,2,2-trifluoro-1-methylethyl, methylsulfanylmethyl, trifluoromethylsulfanylmethyl, trifluoromethoxymethyl, CH₂CN, and CH₂CF₃.

Preferred meanings of the variable R³ are selected from the radicals R3.1, R3.2, R3.3, R3.4, R3.5, R3.6, R3.7, R3.8, R3.9, R3.10, R3.11, R3.12, R3.13, R3.14, R3.15, R3.16, R3.17, R3.18, R3.19, R3.20, R3.21, R3.22, R3.23, R3.24, R3.25, R3.26, R3.27, R3.28, R3.29, R3.30, R3.31, R3.32, R3.33, R3.34, R3.35, R3.36, R3.37, R3.38, R3.39, R3.40, R3.41, R3.42, R3.43, R3.44, R3.45, R3.46, R3.47 and R3.48 shown below:

# denotes the point of attachment to the remainder of the molecule.

Particularly suitable for the mixtures according to the invention are compounds of the formula I in which R⁴ is C₁-C₄-alkyl or C₁-C₄-haloalkyl, in particular C₁-C₄-fluoroalkyl. More preferably, R⁴ is CH₃, C₂H₅, CHF₂ or CF₃, especially CH₃.

Particularly suitable for the mixtures according to the invention are compounds of the formula I in which the variables R³ and R⁴ together with the carbon atom, to which they are attached, form a monocyclic three-, four-, five- or six-membered carbo- or heterocycle, which may contain 1 or 2 heteroatom moieties selected from N—R^(c), O, and S(O)_(k), with k being 0, 1 or 2, which monocyclic three- to six-membered carbo- or heterocycle is unsubstituted or may be substituted by 1, 2, 3 or 4 radicals R^(a3). R^(c) preferably denotes C₁-C₂-alkyl, particularly CH₃, or C₁-C₂-alkylcarbonyl, particularly acetyl. R^(a3) is preferably selected from C₁-C₂-alkyl and halogen, even more preferably C₁-C₂-alkyl and fluorine. If R³ and R⁴ together with the carbon atom, to which they are attached, form a monocyclic three-, four-, five- or six-membered heterocycle, the heterocycle preferably comprises 1 or 2 heteroatom moieties selected from 0 and NR^(c). R^(c) has one of the meanings given above. More preferably, R³ and R⁴ together with the carbon atom, to which they are attached, form C₃-C₆-cycloalkyl such as cyclopropyl, cyclopentyl or cyclohexyl, 2,2-difluorocyclopropyl, 2,2-dichlorocyclopropyl, oxan-4-yl, 1,3-dioxan-5-yl or 2,2-dimethyl-1,3-dioxan-5-yl.

Preferred meanings of the variable R³ and R⁴ taken together are selected from the groups R3.49, R3.50, R3.51, R3.52 and R3.53 shown below:

(CH₂)₂ (R3.49), (CH₂)₄ (R3.50), (CH₂)₅ (R3.51), —CH₂OCH₂OCH₂— (R3.52), and —CH₂OC(CH₃)₂OCH₂— (R3.53).

Particularly suitable for the mixtures according to the invention are compounds of the formula I in which the variables R³ and R⁴ together with the carbon atom, to which they are attached, form a monospiro or dispiro 5-, 6-, 7-, 8-, 9- or 10-membered carbo- or heterocycle, which may contain 1 or 2 heteroatom moieties selected from NR^(c), O, and S(O)_(k), with k being 0, 1 or 2, which monospiro or dispiro 5- to 10-membered carbo- or heterocycle is unsubstituted or may be substituted by 1, 2, 3 or 4 radicals R^(a3). R^(a3), if present, is preferably selected from CN, C₁-C₂-haloalkyl, C₁-C₂-alkylidene and C₁-C₂-alkoxy-C₁-C₂-alkyl. In another embodiment R^(a3) is haloalkyl, preferably CHF₂, or CF₃, preferred CF₃. Substituents R^(a3) are preferably in 1- or 4-position, if the carbocycle is monosubstituted and in 4,4-position, if the carbocycle is disubstituted. More preferably, R³ and R⁴ together with the carbon atom, to which they are attached, form a monospiro or dispiro 5-, 6-, 7-, 8-, 9- or 10-membered carbocycle which is unsubstituted or substituted by 1 or 2 radicals R^(a3). Even more preferably, R³ and R⁴ together with the carbon atom, to which they are attached, form spiro[2.2]pentyl, which is unsubstituted or carries 1 or 2 radicals R^(a3) or 7-dispiro[2.0.1.2]-heptyl which is unsubstituted or carries a radical R^(a3). Specially, R³ and R⁴ together with the carbon atom, to which they are attached, form a radical selected from spiro [2.2]pentyl, 2-methylene-spiro[2.2]pentyl, 1-CN-spiro[2.2]pentyl, 1-CF₃-spiro[2.2]pentyl, 4-CH₃-spiro[2.2]pentyl, 4,4-(CH₃)₂-spiro[2.2]pentyl, 4-(CH₂OCH₃)-spiro[2.2]pentyl, 4-(CF₃)-spiro[2.2]pentyl and 7-dispiro[2.0.1.2]-heptyl.

Preferred meanings of the variable R³ and R⁴ together with the carbon atom, to which they are attached, form a monospiro or dispiro carbocycle, which is unsubstituted or substituted are selected from the radicals R3.54, R3.55, R3.56, R3.57, R3.58, R3.59, R3.60, R3.61 and R3.62 shown below:

where # denotes the point of attachment to the remainder of the molecule.

Particularly suitable for the mixtures according to the invention are compounds of the formula I in which the variable R⁵ is H, CN, C₁-C₂-alkyl, C₁-C₂-alkoxy, C₁-C₂-alkylsulfanyl, C₁-C₂-haloalkyl, especially C₁-C₂-fluoroalkyl or C₁-C₂-haloalkylsulfanyl, especially C₁-C₂-fluoroalkyl. More preferably, R⁵ is H, CH₃, CN, F, OCH₃, SCH₃, CF₃, OCF₃, or SCF₃. Most preferably R⁵ is H, or CN, especially H.

Examples of preferred compounds are compounds of the formula I, where the variables have one of the general or preferred meanings given above. Especially preferred with a view to their use are the compounds I compiled in the tables I, II, III, and IV below. Moreover, the meanings mentioned below for the individual variables in the tables are per se, independently of the combination in which they are mentioned, a particularly preferred embodiment of the substituents in question.

TABLE I No. R¹ R² R³ R⁴ R⁵ I-1 CH₃ CH₃ R3.1 CH₃ H I-2 C₂H₅ CH₃ R3.1 CH₃ H I-3 CH₃ CH₂F R3.1 CH₃ H I-4 C₂H₅ CH₂F R3.1 CH₃ H I-5 CH₃ CF₃ R3.1 CH₃ H I-6 C₂H₅ CF₃ R3.1 CH₃ H I-7 CH₃ CH₃ R3.2 CH₃ H I-8 C₂H₅ CH₃ R3.2 CH₃ H I-9 CH₃ CH₂F R3.2 CH₃ H I-10 C₂H₅ CH₂F R3.2 CH₃ H I-11 CH₃ CF₃ R3.2 CH₃ H I-12 C₂H₅ CF₃ R3.2 CH₃ H I-13 CH₃ CH₃ R3.3 CH₃ H I-14 C₂H₅ CH₃ R3.3 CH₃ H I-15 CH₃ CH₂F R3.3 CH₃ H I-16 C₂H₅ CH₂F R3.3 CH₃ H I-17 CH₃ CF₃ R3.3 CH₃ H I-18 C₂H₅ CF₃ R3.3 CH₃ H I-19 CH₃ CH₃ R3.4 CH₃ H I-20 C₂H₅ CH₃ R3.4 CH₃ H I-21 CH₃ CH₂F R3.4 CH₃ H I-22 C₂H₅ CH₂F R3.4 CH₃ H I-23 CH₃ CF₃ R3.4 CH₃ H I-24 C₂H₅ CF₃ R3.4 CH₃ H I-25 CH₃ CH₃ R3.5 CH₃ H I-26 C₂H₅ CH₃ R3.5 CH₃ H I-27 CH₃ CH₂F R3.5 CH₃ H I-28 C₂H₅ CH₂F R3.5 CH₃ H I-29 CH₃ CF₃ R3.5 CH₃ H I-30 C₂H₅ CF₃ R3.5 CH₃ H I-31 CH₃ CH₃ R3.6 CH₃ H I-32 C₂H₅ CH₃ R3.6 CH₃ H I-33 CH₃ CH₂F R3.6 CH₃ H I-34 C₂H₅ CH₂F R3.6 CH₃ H I-35 CH₃ CF₃ R3.6 CH₃ H I-36 C₂H₅ CF₃ R3.6 CH₃ H I-37 CH₃ CH₃ R3.7 CH₃ H I-38 C₂H₅ CH₃ R3.7 CH₃ H I-39 CH₃ CH₂F R3.7 CH₃ H I-40 C₂H₅ CH₂F R3.7 CH₃ H I-41 CH₃ CF₃ R3.7 CH₃ H I-42 C₂H₅ CF₃ R3.7 CH₃ H I-43 CH₃ CH₃ R3.8 CH₃ H I-44 C₂H₅ CH₃ R3.8 CH₃ H I-45 CH₃ CH₂F R3.8 CH₃ H I-46 C₂H₅ CH₂F R3.8 CH₃ H I-47 CH₃ CF₃ R3.8 CH₃ H I-48 C₂H₅ CF₃ R3.8 CH₃ H I-49 CH₃ CH₃ R3.9 CH₃ H I-50 C₂H₅ CH₃ R3.9 CH₃ H I-51 CH₃ CH₂F R3.9 CH₃ H I-52 C₂H₅ CH₂F R3.9 CH₃ H I-53 CH₃ CF₃ R3.9 CH₃ H I-54 C₂H₅ CF₃ R3.9 CH₃ H I-55 CH₃ CH₃ R3.1 C₂H₅ H I-56 C₂H₅ CH₃ R3.1 C₂H₅ H I-57 CH₃ CH₂F R3.1 C₂H₅ H I-58 C₂H₅ CH₂F R3.1 C₂H₅ H I-59 CH₃ CF₃ R3.1 C₂H₅ H I-60 C₂H₅ CF₃ R3.1 C₂H₅ H I-61 CH₃ CH₃ R3.2 C₂H₅ H I-62 C₂H₅ CH₃ R3.2 C₂H₅ H I-63 CH₃ CH₂F R3.2 C₂H₅ H I-64 C₂H₅ CH₂F R3.2 C₂H₅ H I-65 CH₃ CF₃ R3.2 C₂H₅ H I-66 C₂H₅ CF₃ R3.2 C₂H₅ H I-67 CH₃ CH₃ R3.3 C₂H₅ H I-68 C₂H₅ CH₃ R3.3 C₂H₅ H I-69 CH₃ CH₂F R3.3 C₂H₅ H I-70 C₂H₅ CH₂F R3.3 C₂H₅ H I-71 CH₃ CF₃ R3.3 C₂H₅ H I-72 C₂H₅ CF₃ R3.3 C₂H₅ H I-73 CH₃ CH₃ R3.4 C₂H₅ H I-74 C₂H₅ CH₃ R3.4 C₂H₅ H I-75 CH₃ CH₂F R3.4 C₂H₅ H I-76 C₂H₅ CH₂F R3.4 C₂H₅ H I-77 CH₃ CF₃ R3.4 C₂H₅ H I-78 C₂H₅ CF₃ R3.4 C₂H₅ H I-79 CH₃ CH₃ R3.5 C₂H₅ H I-80 C₂H₅ CH₃ R3.5 C₂H₅ H I-81 CH₃ CH₂F R3.5 C₂H₅ H I-82 C₂H₅ CH₂F R3.5 C₂H₅ H I-83 CH₃ CF₃ R3.5 C₂H₅ H I-84 C₂H₅ CF₃ R3.5 C₂H₅ H I-85 CH₃ CH₃ R3.6 C₂H₅ H I-86 C₂H₅ CH₃ R3.6 C₂H₅ H I-87 CH₃ CH₂F R3.6 C₂H₅ H I-88 C₂H₅ CH₂F R3.6 C₂H₅ H I-89 CH₃ CF₃ R3.6 C₂H₅ H I-90 C₂H₅ CF₃ R3.6 C₂H₅ H I-91 CH₃ CH₃ R3.7 C₂H₅ H I-92 C₂H₅ CH₃ R3.7 C₂H₅ H I-93 CH₃ CH₂F R3.7 C₂H₅ H I-94 C₂H₅ CH₂F R3.7 C₂H₅ H I-95 CH₃ CF₃ R3.7 C₂H₅ H I-96 C₂H₅ CF₃ R3.7 C₂H₅ H I-97 CH₃ CH₃ R3.8 C₂H₅ H I-98 C₂H₅ CH₃ R3.8 C₂H₅ H I-99 CH₃ CH₂F R3.8 C₂H₅ H I-100 C₂H₅ CH₂F R3.8 C₂H₅ H I-101 CH₃ CF₃ R3.8 C₂H₅ H I-102 C₂H₅ CF₃ R3.8 C₂H₅ H I-103 CH₃ CH₃ R3.9 C₂H₅ H I-104 C₂H₅ CH₃ R3.9 C₂H₅ H I-105 CH₃ CH₂F R3.9 C₂H₅ H I-106 C₂H₅ CH₂F R3.9 C₂H₅ H I-107 CH₃ CF₃ R3.9 C₂H₅ H I-108 C₂H₅ CF₃ R3.9 C₂H₅ H I-109 CH₃ CH₃ R3.1 CF₃ H I-110 C₂H₅ CH₃ R3.1 CF₃ H I-111 CH₃ CH₂F R3.1 CF₃ H I-112 C₂H₅ CH₂F R3.1 CF₃ H I-113 CH₃ CF₃ R3.1 CF₃ H I-114 C₂H₅ CF₃ R3.1 CF₃ H I-115 CH₃ CH₃ R3.2 CF₃ H I-116 C₂H₅ CH₃ R3.2 CF₃ H I-117 CH₃ CH₂F R3.2 CF₃ H I-118 C₂H₅ CH₂F R3.2 CF₃ H I-119 CH₃ CF₃ R3.2 CF₃ H I-120 C₂H₅ CF₃ R3.2 CF₃ H I-121 CH₃ CH₃ R3.3 CF₃ H I-122 C₂H₅ CH₃ R3.3 CF₃ H I-123 CH₃ CH₂F R3.3 CF₃ H I-124 C₂H₅ CH₂F R3.3 CF₃ H I-125 CH₃ CF₃ R3.3 CF₃ H I-126 C₂H₅ CF₃ R3.3 CF₃ H I-127 CH₃ CH₃ R3.4 CF₃ H I-128 C₂H₅ CH₃ R3.4 CF₃ H I-129 CH₃ CH₂F R3.4 CF₃ H I-130 C₂H₅ CH₂F R3.4 CF₃ H I-131 CH₃ CF₃ R3.4 CF₃ H I-132 C₂H₅ CF₃ R3.4 CF₃ H I-133 CH₃ CH₃ R3.5 CF₃ H I-134 C₂H₅ CH₃ R3.5 CF₃ H I-135 CH₃ CH₂F R3.5 CF₃ H I-136 C₂H₅ CH₂F R3.5 CF₃ H I-137 CH₃ CF₃ R3.5 CF₃ H I-138 C₂H₅ CF₃ R3.5 CF₃ H I-139 CH₃ CH₃ R3.6 CF₃ H I-140 C₂H₅ CH₃ R3.6 CF₃ H I-141 CH₃ CH₂F R3.6 CF₃ H I-142 C₂H₅ CH₂F R3.6 CF₃ H I-143 CH₃ CF₃ R3.6 CF₃ H I-144 C₂H₅ CF₃ R3.6 CF₃ H I-145 CH₃ CH₃ R3.7 CF₃ H I-146 C₂H₅ CH₃ R3.7 CF₃ H I-147 CH₃ CH₂F R3.7 CF₃ H I-148 C₂H₅ CH₂F R3.7 CF₃ H I-149 CH₃ CF₃ R3.7 CF₃ H I-150 C₂H₅ CF₃ R3.7 CF₃ H I-151 CH₃ CH₃ R3.8 CF₃ H I-152 C₂H₅ CH₃ R3.8 CF₃ H I-153 CH₃ CH₂F R3.8 CF₃ H I-154 C₂H₅ CH₂F R3.8 CF₃ H I-155 CH₃ CF₃ R3.8 CF₃ H I-156 C₂H₅ CF₃ R3.8 CF₃ H I-157 CH₃ CH₃ R3.9 CF₃ H I-158 C₂H₅ CH₃ R3.9 CF₃ H I-159 CH₃ CH₂F R3.9 CF₃ H I-160 C₂H₅ CH₂F R3.9 CF₃ H I-161 CH₃ CF₃ R3.9 CF₃ H I-162 C₂H₅ CF₃ R3.9 CF₃ H I-163 CH₃ CH₃ R3.1 CHF₂ H I-164 C₂H₅ CH₃ R3.1 CHF₂ H I-165 CH₃ CH₂F R3.1 CHF₂ H I-166 C₂H₅ CH₂F R3.1 CHF₂ H I-167 CH₃ CF₃ R3.1 CHF₂ H I-168 C₂H₅ CF₃ R3.1 CHF₂ H I-169 CH₃ CH₃ R3.2 CHF₂ H I-170 C₂H₅ CH₃ R3.2 CHF₂ H I-171 CH₃ CH₂F R3.2 CHF₂ H I-172 C₂H₅ CH₂F R3.2 CHF₂ H I-173 CH₃ CF₃ R3.2 CHF₂ H I-174 C₂H₅ CF₃ R3.2 CHF₂ H I-175 CH₃ CH₃ R3.3 CHF₂ H I-176 C₂H₅ CH₃ R3.3 CHF₂ H I-177 CH₃ CH₂F R3.3 CHF₂ H I-178 C₂H₅ CH₂F R3.3 CHF₂ H I-179 CH₃ CF₃ R3.3 CHF₂ H I-180 C₂H₅ CF₃ R3.3 CHF₂ H I-181 CH₃ CH₃ R3.4 CHF₂ H I-182 C₂H₅ CH₃ R3.4 CHF₂ H I-183 CH₃ CH₂F R3.4 CHF₂ H I-184 C₂H₅ CH₂F R3.4 CHF₂ H I-185 CH₃ CF₃ R3.4 CHF₂ H I-186 C₂H₅ CF₃ R3.4 CHF₂ H I-187 CH₃ CH₃ R3.5 CHF₂ H I-188 C₂H₅ CH₃ R3.5 CHF₂ H I-189 CH₃ CH₂F R3.5 CHF₂ H I-190 C₂H₅ CH₂F R3.5 CHF₂ H I-191 CH₃ CF₃ R3.5 CHF₂ H I-192 C₂H₅ CF₃ R3.5 CHF₂ H I-193 CH₃ CH₃ R3.6 CHF₂ H I-194 C₂H₅ CH₃ R3.6 CHF₂ H I-195 CH₃ CH₂F R3.6 CHF₂ H I-196 C₂H₅ CH₂F R3.6 CHF₂ H I-197 CH₃ CF₃ R3.6 CHF₂ H I-198 C₂H₅ CF₃ R3.6 CHF₂ H I-199 CH₃ CH₃ R3.7 CHF₂ H I-200 C₂H₅ CH₃ R3.7 CHF₂ H I-201 CH₃ CH₂F R3.7 CHF₂ H I-202 C₂H₅ CH₂F R3.7 CHF₂ H I-203 CH₃ CF₃ R3.7 CHF₂ H I-204 C₂H₅ CF₃ R3.7 CHF₂ H I-205 CH₃ CH₃ R3.8 CHF₂ H I-206 C₂H₅ CH₃ R3.8 CHF₂ H I-207 CH₃ CH₂F R3.8 CHF₂ H I-208 C₂H₅ CH₂F R3.8 CHF₂ H I-209 CH₃ CF₃ R3.8 CHF₂ H I-210 C₂H₅ CF₃ R3.8 CHF₂ H I-211 CH₃ CH₃ R3.9 CHF₂ H I-212 C₂H₅ CH₃ R3.9 CHF₂ H I-213 CH₃ CH₂F R3.9 CHF₂ H I-214 C₂H₅ CH₂F R3.9 CHF₂ H I-215 CH₃ CF₃ R3.9 CHF₂ H I-216 C₂H₅ CF₃ R3.9 CHF₂ H I-217 CH₃ CH₃ R3.1 CH₃ CH₃ I-218 C₂H₅ CH₃ R3.1 CH₃ CH₃ I-219 CH₃ CH₂F R3.1 CH₃ CH₃ I-220 C₂H₅ CH₂F R3.1 CH₃ CH₃ I-221 CH₃ CF₃ R3.1 CH₃ CH₃ I-222 C₂H₅ CF₃ R3.1 CH₃ CH₃ I-223 CH₃ CH₃ R3.2 CH₃ CH₃ I-224 C₂H₅ CH₃ R3.2 CH₃ CH₃ I-225 CH₃ CH₂F R3.2 CH₃ CH₃ I-226 C₂H₅ CH₂F R3.2 CH₃ CH₃ I-227 CH₃ CF₃ R3.2 CH₃ CH₃ I-228 C₂H₅ CF₃ R3.2 CH₃ CH₃ I-229 CH₃ CH₃ R3.3 CH₃ CH₃ I-230 C₂H₅ CH₃ R3.3 CH₃ CH₃ I-231 CH₃ CH₂F R3.3 CH₃ CH₃ I-232 C₂H₅ CH₂F R3.3 CH₃ CH₃ I-233 CH₃ CF₃ R3.3 CH₃ CH₃ I-234 C₂H₅ CF₃ R3.3 CH₃ CH₃ I-235 CH₃ CH₃ R3.4 CH₃ CH₃ I-236 C₂H₅ CH₃ R3.4 CH₃ CH₃ I-237 CH₃ CH₂F R3.4 CH₃ CH₃ I-238 C₂H₅ CH₂F R3.4 CH₃ CH₃ I-239 CH₃ CF₃ R3.4 CH₃ CH₃ I-240 C₂H₅ CF₃ R3.4 CH₃ CH₃ I-241 CH₃ CH₃ R3.5 CH₃ CH₃ I-242 C₂H₅ CH₃ R3.5 CH₃ CH₃ I-243 CH₃ CH₂F R3.5 CH₃ CH₃ I-244 C₂H₅ CH₂F R3.5 CH₃ CH₃ I-245 CH₃ CF₃ R3.5 CH₃ CH₃ I-246 C₂H₅ CF₃ R3.5 CH₃ CH₃ I-247 CH₃ CH₃ R3.6 CH₃ CH₃ I-248 C₂H₅ CH₃ R3.6 CH₃ CH₃ I-249 CH₃ CH₂F R3.6 CH₃ CH₃ I-250 C₂H₅ CH₂F R3.6 CH₃ CH₃ I-251 CH₃ CF₃ R3.6 CH₃ CH₃ I-252 C₂H₅ CF₃ R3.6 CH₃ CH₃ I-253 CH₃ CH₃ R3.7 CH₃ CH₃ I-254 C₂H₅ CH₃ R3.7 CH₃ CH₃ I-255 CH₃ CH₂F R3.7 CH₃ CH₃ I-256 C₂H₅ CH₂F R3.7 CH₃ CH₃ I-257 CH₃ CF₃ R3.7 CH₃ CH₃ I-258 C₂H₅ CF₃ R3.7 CH₃ CH₃ I-259 CH₃ CH₃ R3.8 CH₃ CH₃ I-260 C₂H₅ CH₃ R3.8 CH₃ CH₃ I-261 CH₃ CH₂F R3.8 CH₃ CH₃ I-262 C₂H₅ CH₂F R3.8 CH₃ CH₃ I-263 CH₃ CF₃ R3.8 CH₃ CH₃ I-264 C₂H₅ CF₃ R3.8 CH₃ CH₃ I-265 CH₃ CH₃ R3.9 CH₃ CH₃ I-266 C₂H₅ CH₃ R3.9 CH₃ CH₃ I-267 CH₃ CH₂F R3.9 CH₃ CH₃ I-268 C₂H₅ CH₂F R3.9 CH₃ CH₃ I-269 CH₃ CF₃ R3.9 CH₃ CH₃ I-270 C₂H₅ CF₃ R3.9 CH₃ CH₃ I-271 CH₃ CH₃ R3.1 C₂H₅ CH₃ I-272 C₂H₅ CH₃ R3.1 C₂H₅ CH₃ I-273 CH₃ CH₂F R3.1 C₂H₅ CH₃ I-274 C₂H₅ CH₂F R3.1 C₂H₅ CH₃ I-275 CH₃ CF₃ R3.1 C₂H₅ CH₃ I-276 C₂H₅ CF₃ R3.1 C₂H₅ CH₃ I-277 CH₃ CH₃ R3.2 C₂H₅ CH₃ I-278 C₂H₅ CH₃ R3.2 C₂H₅ CH₃ I-279 CH₃ CH₂F R3.2 C₂H₅ CH₃ I-280 C₂H₅ CH₂F R3.2 C₂H₅ CH₃ I-281 CH₃ CF₃ R3.2 C₂H₅ CH₃ I-282 C₂H₅ CF₃ R3.2 C₂H₅ CH₃ I-283 CH₃ CH₃ R3.3 C₂H₅ CH₃ I-284 C₂H₅ CH₃ R3.3 C₂H₅ CH₃ I-285 CH₃ CH₂F R3.3 C₂H₅ CH₃ I-286 C₂H₅ CH₂F R3.3 C₂H₅ CH₃ I-287 CH₃ CF₃ R3.3 C₂H₅ CH₃ I-288 C₂H₅ CF₃ R3.3 C₂H₅ CH₃ I-289 CH₃ CH₃ R3.4 C₂H₅ CH₃ I-290 C₂H₅ CH₃ R3.4 C₂H₅ CH₃ I-291 CH₃ CH₂F R3.4 C₂H₅ CH₃ I-292 C₂H₅ CH₂F R3.4 C₂H₅ CH₃ I-293 CH₃ CF₃ R3.4 C₂H₅ CH₃ I-294 C₂H₅ CF₃ R3.4 C₂H₅ CH₃ I-295 CH₃ CH₃ R3.5 C₂H₅ CH₃ I-296 C₂H₅ CH₃ R3.5 C₂H₅ CH₃ I-297 CH₃ CH₂F R3.5 C₂H₅ CH₃ I-298 C₂H₅ CH₂F R3.5 C₂H₅ CH₃ I-299 CH₃ CF₃ R3.5 C₂H₅ CH₃ I-300 C₂H₅ CF₃ R3.5 C₂H₅ CH₃ I-301 CH₃ CH₃ R3.6 C₂H₅ CH₃ I-302 C₂H₅ CH₃ R3.6 C₂H₅ CH₃ I-303 CH₃ CH₂F R3.6 C₂H₅ CH₃ I-304 C₂H₅ CH₂F R3.6 C₂H₅ CH₃ I-305 CH₃ CF₃ R3.6 C₂H₅ CH₃ I-306 C₂H₅ CF₃ R3.6 C₂H₅ CH₃ I-307 CH₃ CH₃ R3.7 C₂H₅ CH₃ I-308 C₂H₅ CH₃ R3.7 C₂H₅ CH₃ I-309 CH₃ CH₂F R3.7 C₂H₅ CH₃ I-310 C₂H₅ CH₂F R3.7 C₂H₅ CH₃ I-311 CH₃ CF₃ R3.7 C₂H₅ CH₃ I-312 C₂H₅ CF₃ R3.7 C₂H₅ CH₃ I-313 CH₃ CH₃ R3.8 C₂H₅ CH₃ I-314 C₂H₅ CH₃ R3.8 C₂H₅ CH₃ I-315 CH₃ CH₂F R3.8 C₂H₅ CH₃ I-316 C₂H₅ CH₂F R3.8 C₂H₅ CH₃ I-317 CH₃ CF₃ R3.8 C₂H₅ CH₃ I-318 C₂H₅ CF₃ R3.8 C₂H₅ CH₃ I-319 CH₃ CH₃ R3.9 C₂H₅ CH₃ I-320 C₂H₅ CH₃ R3.9 C₂H₅ CH₃ I-321 CH₃ CH₂F R3.9 C₂H₅ CH₃ I-322 C₂H₅ CH₂F R3.9 C₂H₅ CH₃ I-323 CH₃ CF₃ R3.9 C₂H₅ CH₃ I-324 C₂H₅ CF₃ R3.9 C₂H₅ CH₃ I-325 CH₃ CH₃ R3.1 CF₃ CH₃ I-326 C₂H₅ CH₃ R3.1 CF₃ CH₃ I-327 CH₃ CH₂F R3.1 CF₃ CH₃ I-328 C₂H₅ CH₂F R3.1 CF₃ CH₃ I-329 CH₃ CF₃ R3.1 CF₃ CH₃ I-330 C₂H₅ CF₃ R3.1 CF₃ CH₃ I-331 CH₃ CH₃ R3.2 CF₃ CH₃ I-332 C₂H₅ CH₃ R3.2 CF₃ CH₃ I-333 CH₃ CH₂F R3.2 CF₃ CH₃ I-334 C₂H₅ CH₂F R3.2 CF₃ CH₃ I-335 CH₃ CF₃ R3.2 CF₃ CH₃ I-336 C₂H₅ CF₃ R3.2 CF₃ CH₃ I-337 CH₃ CH₃ R3.3 CF₃ CH₃ I-338 C₂H₅ CH₃ R3.3 CF₃ CH₃ I-339 CH₃ CH₂F R3.3 CF₃ CH₃ I-340 C₂H₅ CH₂F R3.3 CF₃ CH₃ I-341 CH₃ CF₃ R3.3 CF₃ CH₃ I-342 C₂H₅ CF₃ R3.3 CF₃ CH₃ I-343 CH₃ CH₃ R3.4 CF₃ CH₃ I-344 C₂H₅ CH₃ R3.4 CF₃ CH₃ I-345 CH₃ CH₂F R3.4 CF₃ CH₃ I-346 C₂H₅ CH₂F R3.4 CF₃ CH₃ I-347 CH₃ CF₃ R3.4 CF₃ CH₃ I-348 C₂H₅ CF₃ R3.4 CF₃ CH₃ I-349 CH₃ CH₃ R3.5 CF₃ CH₃ I-350 C₂H₅ CH₃ R3.5 CF₃ CH₃ I-351 CH₃ CH₂F R3.5 CF₃ CH₃ I-352 C₂H₅ CH₂F R3.5 CF₃ CH₃ I-353 CH₃ CF₃ R3.5 CF₃ CH₃ I-354 C₂H₅ CF₃ R3.5 CF₃ CH₃ I-355 CH₃ CH₃ R3.6 CF₃ CH₃ I-356 C₂H₅ CH₃ R3.6 CF₃ CH₃ I-357 CH₃ CH₂F R3.6 CF₃ CH₃ I-358 C₂H₅ CH₂F R3.6 CF₃ CH₃ I-359 CH₃ CF₃ R3.6 CF₃ CH₃ I-360 C₂H₅ CF₃ R3.6 CF₃ CH₃ I-361 CH₃ CH₃ R3.7 CF₃ CH₃ I-362 C₂H₅ CH₃ R3.7 CF₃ CH₃ I-363 CH₃ CH₂F R3.7 CF₃ CH₃ I-364 C₂H₅ CH₂F R3.7 CF₃ CH₃ I-365 CH₃ CF₃ R3.7 CF₃ CH₃ I-366 C₂H₅ CF₃ R3.7 CF₃ CH₃ I-367 CH₃ CH₃ R3.8 CF₃ CH₃ I-368 C₂H₅ CH₃ R3.8 CF₃ CH₃ I-369 CH₃ CH₂F R3.8 CF₃ CH₃ I-370 C₂H₅ CH₂F R3.8 CF₃ CH₃ I-371 CH₃ CF₃ R3.8 CF₃ CH₃ I-372 C₂H₅ CF₃ R3.8 CF₃ CH₃ I-373 CH₃ CH₃ R3.9 CF₃ CH₃ I-374 C₂H₅ CH₃ R3.9 CF₃ CH₃ I-375 CH₃ CH₂F R3.9 CF₃ CH₃ I-376 C₂H₅ CH₂F R3.9 CF₃ CH₃ I-377 CH₃ CF₃ R3.9 CF₃ CH₃ I-378 C₂H₅ CF₃ R3.9 CF₃ CH₃ I-379 CH₃ CH₃ R3.1 CHF₂ CH₃ I-380 C₂H₅ CH₃ R3.1 CHF₂ CH₃ I-381 CH₃ CH₂F R3.1 CHF₂ CH₃ I-382 C₂H₅ CH₂F R3.1 CHF₂ CH₃ I-383 CH₃ CF₃ R3.1 CHF₂ CH₃ I-384 C₂H₅ CF₃ R3.1 CHF₂ CH₃ I-385 CH₃ CH₃ R3.2 CHF₂ CH₃ I-386 C₂H₅ CH₃ R3.2 CHF₂ CH₃ I-387 CH₃ CH₂F R3.2 CHF₂ CH₃ I-388 C₂H₅ CH₂F R3.2 CHF₂ CH₃ I-389 CH₃ CF₃ R3.2 CHF₂ CH₃ I-390 C₂H₅ CF₃ R3.2 CHF₂ CH₃ I-391 CH₃ CH₃ R3.3 CHF₂ CH₃ I-392 C₂H₅ CH₃ R3.3 CHF₂ CH₃ I-393 CH₃ CH₂F R3.3 CHF₂ CH₃ I-394 C₂H₅ CH₂F R3.3 CHF₂ CH₃ I-395 CH₃ CF₃ R3.3 CHF₂ CH₃ I-396 C₂H₅ CF₃ R3.3 CHF₂ CH₃ I-397 CH₃ CH₃ R3.4 CHF₂ CH₃ I-398 C₂H₅ CH₃ R3.4 CHF₂ CH₃ I-399 CH₃ CH₂F R3.4 CHF₂ CH₃ I-400 C₂H₅ CH₂F R3.4 CHF₂ CH₃ I-401 CH₃ CF₃ R3.4 CHF₂ CH₃ I-402 C₂H₅ CF₃ R3.4 CHF₂ CH₃ I-403 CH₃ CH₃ R3.5 CHF₂ CH₃ I-404 C₂H₅ CH₃ R3.5 CHF₂ CH₃ I-405 CH₃ CH₂F R3.5 CHF₂ CH₃ I-406 C₂H₅ CH₂F R3.5 CHF₂ CH₃ I-407 CH₃ CF₃ R3.5 CHF₂ CH₃ I-408 C₂H₅ CF₃ R3.5 CHF₂ CH₃ I-409 CH₃ CH₃ R3.6 CHF₂ CH₃ I-410 C₂H₅ CH₃ R3.6 CHF₂ CH₃ I-411 CH₃ CH₂F R3.6 CHF₂ CH₃ I-412 C₂H₅ CH₂F R3.6 CHF₂ CH₃ I-413 CH₃ CF₃ R3.6 CHF₂ CH₃ I-414 C₂H₅ CF₃ R3.6 CHF₂ CH₃ I-415 CH₃ CH₃ R3.7 CHF₂ CH₃ I-416 C₂H₅ CH₃ R3.7 CHF₂ CH₃ I-417 CH₃ CH₂F R3.7 CHF₂ CH₃ I-418 C₂H₅ CH₂F R3.7 CHF₂ CH₃ I-419 CH₃ CF₃ R3.7 CHF₂ CH₃ I-420 C₂H₅ CF₃ R3.7 CHF₂ CH₃ I-421 CH₃ CH₃ R3.8 CHF₂ CH₃ I-422 C₂H₅ CH₃ R3.8 CHF₂ CH₃ I-423 CH₃ CH₂F R3.8 CHF₂ CH₃ I-424 C₂H₅ CH₂F R3.8 CHF₂ CH₃ I-425 CH₃ CF₃ R3.8 CHF₂ CH₃ I-426 C₂H₅ CF₃ R3.8 CHF₂ CH₃ I-427 CH₃ CH₃ R3.9 CHF₂ CH₃ I-428 C₂H₅ CH₃ R3.9 CHF₂ CH₃ I-429 CH₃ CH₂F R3.9 CHF₂ CH₃ I-430 C₂H₅ CH₂F R3.9 CHF₂ CH₃ I-431 CH₃ CF₃ R3.9 CHF₂ CH₃ I-432 C₂H₅ CF₃ R3.9 CHF₂ CH₃

TABLE II No. R¹ R² R³ R⁴ R⁵ I-433 CH₃ CH₃ R3.10 CHF₂ H I-434 C₂H₅ CH₃ R3.10 CHF₂ H I-435 CH₃ CHF₂ R3.10 CHF₂ H I-436 C₂H₅ CHF₂ R3.10 CHF₂ H I-437 CH₃ CF₃ R3.10 CHF₂ H I-438 C₂H₅ CF₃ R3.10 CHF₂ H I-439 CH₃ CH₃ R3.11 CHF₂ H I-440 C₂H₅ CH₃ R3.11 CHF₂ H I-441 CH₃ CHF₂ R3.11 CHF₂ H I-442 C₂H₅ CHF₂ R3.11 CHF₂ H I-443 CH₃ CF₃ R3.11 CHF₂ H I-444 C₂H₅ CF₃ R3.11 CHF₂ H I-445 CH₃ CH₃ R3.12 CHF₂ H I-446 C₂H₅ CH₃ R3.12 CHF₂ H I-447 CH₃ CHF₂ R3.12 CHF₂ H I-448 C₂H₅ CHF₂ R3.12 CHF₂ H I-449 CH₃ CF₃ R3.12 CHF₂ H I-450 C₂H₅ CF₃ R3.12 CHF₂ H I-451 CH₃ CH₃ R3.13 CHF₂ H I-452 C₂H₅ CH₃ R3.13 CHF₂ H I-453 CH₃ CHF₂ R3.13 CHF₂ H I-454 C₂H₅ CHF₂ R3.13 CHF₂ H I-455 CH₃ CF₃ R3.13 CHF₂ H I-456 C₂H₅ CF₃ R3.13 CHF₂ H I-457 CH₃ CH₃ R3.14 CHF₂ H I-458 C₂H₅ CH₃ R3.14 CHF₂ H I-459 CH₃ CHF₂ R3.14 CHF₂ H I-460 C₂H₅ CHF₂ R3.14 CHF₂ H I-461 CH₃ CF₃ R3.14 CHF₂ H I-462 C₂H₅ CF₃ R3.14 CHF₂ H I-463 CH₃ CH₃ R3.15 CHF₂ H I-464 C₂H₅ CH₃ R3.15 CHF₂ H I-465 CH₃ CHF₂ R3.15 CHF₂ H I-466 C₂H₅ CHF₂ R3.15 CHF₂ H I-467 CH₃ CF₃ R3.15 CHF₂ H I-468 C₂H₅ CF₃ R3.15 CHF₂ H I-469 CH₃ CH₃ R3.16 CHF₂ H I-470 C₂H₅ CH₃ R3.16 CHF₂ H I-471 CH₃ CHF₂ R3.16 CHF₂ H I-472 C₂H₅ CHF₂ R3.16 CHF₂ H I-473 CH₃ CF₃ R3.16 CHF₂ H I-474 C₂H₅ CF₃ R3.16 CHF₂ H I-475 CH₃ CH₃ R3.17 CHF₂ H I-476 C₂H₅ CH₃ R3.17 CHF₂ H I-477 CH₃ CHF₂ R3.17 CHF₂ H I-478 C₂H₅ CHF₂ R3.17 CHF₂ H I-479 CH₃ CF₃ R3.17 CHF₂ H I-480 C₂H₅ CF₃ R3.17 CHF₂ H I-481 CH₃ CH₃ R3.18 CHF₂ H I-482 C₂H₅ CH₃ R3.18 CHF₂ H I-483 CH₃ CHF₂ R3.18 CHF₂ H I-484 C₂H₅ CHF₂ R3.18 CHF₂ H I-485 CH₃ CF₃ R3.18 CHF₂ H I-486 C₂H₅ CF₃ R3.18 CHF₂ H I-487 CH₃ CH₃ R3.19 CHF₂ H I-488 C₂H₅ CH₃ R3.19 CHF₂ H I-489 CH₃ CHF₂ R3.19 CHF₂ H I-490 C₂H₅ CHF₂ R3.19 CHF₂ H I-491 CH₃ CF₃ R3.19 CHF₂ H I-492 C₂H₅ CF₃ R3.19 CHF₂ H I-493 CH₃ CH₃ R3.20 CHF₂ H I-494 C₂H₅ CH₃ R3.20 CHF₂ H I-495 CH₃ CHF₂ R3.20 CHF₂ H I-496 C₂H₅ CHF₂ R3.20 CHF₂ H I-497 CH₃ CF₃ R3.20 CHF₂ H I-498 C₂H₅ CF₃ R3.20 CHF₂ H I-499 CH₃ CH₃ R3.21 CHF₂ H I-500 C₂H₅ CH₃ R3.21 CHF₂ H I-501 CH₃ CHF₂ R3.21 CHF₂ H I-502 C₂H₅ CHF₂ R3.21 CHF₂ H I-503 CH₃ CF₃ R3.21 CHF₂ H I-504 C₂H₅ CF₃ R3.21 CHF₂ H I-505 CH₃ CH₃ R3.22 CHF₂ H I-506 C₂H₅ CH₃ R3.22 CHF₂ H I-507 CH₃ CHF₂ R3.22 CHF₂ H I-508 C₂H₅ CHF₂ R3.22 CHF₂ H I-509 CH₃ CF₃ R3.22 CHF₂ H I-510 C₂H₅ CF₃ R3.22 CHF₂ H I-511 CH₃ CH₃ R3.23 CHF₂ H I-512 C₂H₅ CH₃ R3.23 CHF₂ H I-513 CH₃ CHF₂ R3.23 CHF₂ H I-514 C₂H₅ CHF₂ R3.23 CHF₂ H I-515 CH₃ CF₃ R3.23 CHF₂ H I-516 C₂H₅ CF₃ R3.23 CHF₂ H I-517 CH₃ CH₃ R3.24 CHF₂ H I-518 C₂H₅ CH₃ R3.24 CHF₂ H I-519 CH₃ CHF₂ R3.24 CHF₂ H I-520 C₂H₅ CHF₂ R3.24 CHF₂ H I-521 CH₃ CF₃ R3.24 CHF₂ H I-522 C₂H₅ CF₃ R3.24 CHF₂ H I-523 CH₃ CH₃ R3.25 CHF₂ H I-524 C₂H₅ CH₃ R3.25 CHF₂ H I-525 CH₃ CHF₂ R3.25 CHF₂ H I-526 C₂H₅ CHF₂ R3.25 CHF₂ H I-527 CH₃ CF₃ R3.25 CHF₂ H I-528 C₂H₅ CF₃ R3.25 CHF₂ H I-529 CH₃ CH₃ R3.26 CHF₂ H I-530 C₂H₅ CH₃ R3.26 CHF₂ H I-531 CH₃ CHF₂ R3.26 CHF₂ H I-532 C₂H₅ CHF₂ R3.26 CHF₂ H I-533 CH₃ CF₃ R3.26 CHF₂ H I-534 C₂H₅ CF₃ R3.26 CHF₂ H I-535 CH₃ CH₃ R3.27 CHF₂ H I-536 C₂H₅ CH₃ R3.27 CHF₂ H I-537 CH₃ CHF₂ R3.27 CHF₂ H I-538 C₂H₅ CHF₂ R3.27 CHF₂ H I-539 CH₃ CF₃ R3.27 CHF₂ H I-540 C₂H₅ CF₃ R3.27 CHF₂ H I-541 CH₃ CH₃ R3.28 CHF₂ H I-542 C₂H₅ CH₃ R3.28 CHF₂ H I-543 CH₃ CHF₂ R3.28 CHF₂ H I-544 C₂H₅ CHF₂ R3.28 CHF₂ H I-545 CH₃ CF₃ R3.28 CHF₂ H I-546 C₂H₅ CF₃ R3.28 CHF₂ H I-547 CH₃ CH₃ R3.29 CHF₂ H I-548 C₂H₅ CH₃ R3.29 CHF₂ H I-549 CH₃ CHF₂ R3.29 CHF₂ H I-550 C₂H₅ CHF₂ R3.29 CHF₂ H I-551 CH₃ CF₃ R3.29 CHF₂ H I-552 C₂H₅ CF₃ R3.29 CHF₂ H I-553 CH₃ CH₃ R3.30 CHF₂ H I-554 C₂H₅ CH₃ R3.30 CHF₂ H I-555 CH₃ CHF₂ R3.30 CHF₂ H I-556 C₂H₅ CHF₂ R3.30 CHF₂ H I-557 CH₃ CF₃ R3.30 CHF₂ H I-558 C₂H₅ CF₃ R3.30 CHF₂ H I-559 CH₃ CH₃ R3.31 CHF₂ H I-560 C₂H₅ CH₃ R3.31 CHF₂ H I-561 CH₃ CHF₂ R3.31 CHF₂ H I-562 C₂H₅ CHF₂ R3.31 CHF₂ H I-563 CH₃ CF₃ R3.31 CHF₂ H I-564 C₂H₅ CF₃ R3.31 CHF₂ H I-565 CH₃ CH₃ R3.32 CHF₂ H I-566 C₂H₅ CH₃ R3.32 CHF₂ H I-567 CH₃ CHF₂ R3.32 CHF₂ H I-568 C₂H₅ CHF₂ R3.32 CHF₂ H I-569 CH₃ CF₃ R3.32 CHF₂ H I-570 C₂H₅ CF₃ R3.32 CHF₂ H I-571 CH₃ CH₃ R3.33 CHF₂ H I-572 C₂H₅ CH₃ R3.33 CHF₂ H I-573 CH₃ CHF₂ R3.33 CHF₂ H I-574 C₂H₅ CHF₂ R3.33 CHF₂ H I-575 CH₃ CF₃ R3.33 CHF₂ H I-576 C₂H₅ CF₃ R3.33 CHF₂ H I-577 CH₃ CH₃ R3.34 CHF₂ H I-578 C₂H₅ CH₃ R3.34 CHF₂ H I-579 CH₃ CHF₂ R3.34 CHF₂ H I-580 C₂H₅ CHF₂ R3.34 CHF₂ H I-581 CH₃ CF₃ R3.34 CHF₂ H I-582 C₂H₅ CF₃ R3.34 CHF₂ H I-583 CH₃ CH₃ R3.35 CHF₂ H I-584 C₂H₅ CH₃ R3.35 CHF₂ H I-585 CH₃ CHF₂ R3.35 CHF₂ H I-586 C₂H₅ CHF₂ R3.35 CHF₂ H I-587 CH₃ CF₃ R3.35 CHF₂ H I-588 C₂H₅ CF₃ R3.35 CHF₂ H I-589 CH₃ CH₃ R3.36 CHF₂ H I-590 C₂H₅ CH₃ R3.36 CHF₂ H I-591 CH₃ CHF₂ R3.36 CHF₂ H I-592 C₂H₅ CHF₂ R3.36 CHF₂ H I-593 CH₃ CF₃ R3.36 CHF₂ H I-594 C₂H₅ CF₃ R3.36 CHF₂ H I-595 CH₃ CH₃ R3.37 CHF₂ H I-596 C₂H₅ CH₃ R3.37 CHF₂ H I-597 CH₃ CHF₂ R3.37 CHF₂ H I-598 C₂H₅ CHF₂ R3.37 CHF₂ H I-599 CH₃ CF₃ R3.37 CHF₂ H I-600 C₂H₅ CF₃ R3.37 CHF₂ H I-601 CH₃ CH₃ R3.38 CHF₂ H I-602 C₂H₅ CH₃ R3.38 CHF₂ H I-603 CH₃ CHF₂ R3.38 CHF₂ H I-604 C₂H₅ CHF₂ R3.38 CHF₂ H I-605 CH₃ CF₃ R3.38 CHF₂ H I-606 C₂H₅ CF₃ R3.38 CHF₂ H I-607 CH₃ CH₃ R3.39 CHF₂ H I-608 C₂H₅ CH₃ R3.39 CHF₂ H I-609 CH₃ CHF₂ R3.39 CHF₂ H I-610 C₂H₅ CHF₂ R3.39 CHF₂ H I-611 CH₃ CF₃ R3.39 CHF₂ H I-612 C₂H₅ CF₃ R3.39 CHF₂ H I-613 CH₃ CH₃ R3.40 CHF₂ H I-614 C₂H₅ CH₃ R3.40 CHF₂ H I-615 CH₃ CHF₂ R3.40 CHF₂ H I-616 C₂H₅ CHF₂ R3.40 CHF₂ H I-617 CH₃ CF₃ R3.40 CHF₂ H I-618 C₂H₅ CF₃ R3.40 CHF₂ H I-619 CH₃ CH₃ R3.41 CHF₂ H I-620 C₂H₅ CH₃ R3.41 CHF₂ H I-621 CH₃ CHF₂ R3.41 CHF₂ H I-622 C₂H₅ CHF₂ R3.41 CHF₂ H I-623 CH₃ CF₃ R3.41 CHF₂ H I-624 C₂H₅ CF₃ R3.41 CHF₂ H I-625 CH₃ CH₃ R3.42 CHF₂ H I-626 C₂H₅ CH₃ R3.42 CHF₂ H I-627 CH₃ CHF₂ R3.42 CHF₂ H I-628 C₂H₅ CHF₂ R3.42 CHF₂ H I-629 CH₃ CF₃ R3.42 CHF₂ H I-630 C₂H₅ CF₃ R3.42 CHF₂ H I-631 CH₃ CH₃ R3.43 CHF₂ H I-632 C₂H₅ CH₃ R3.43 CHF₂ H I-633 CH₃ CHF₂ R3.43 CHF₂ H I-634 C₂H₅ CHF₂ R3.43 CHF₂ H I-635 CH₃ CF₃ R3.43 CHF₂ H I-636 C₂H₅ CF₃ R3.43 CHF₂ H I-637 CH₃ CH₃ R3.44 CHF₂ H I-638 C₂H₅ CH₃ R3.44 CHF₂ H I-639 CH₃ CHF₂ R3.44 CHF₂ H I-640 C₂H₅ CHF₂ R3.44 CHF₂ H I-641 CH₃ CF₃ R3.44 CHF₂ H I-642 C₂H₅ CF₃ R3.44 CHF₂ H I-643 CH₃ CH₃ R3.45 CHF₂ H I-644 C₂H₅ CH₃ R3.45 CHF₂ H I-645 CH₃ CHF₂ R3.45 CHF₂ H I-646 C₂H₅ CHF₂ R3.45 CHF₂ H I-647 CH₃ CF₃ R3.45 CHF₂ H I-648 C₂H₅ CF₃ R3.45 CHF₂ H I-649 CH₃ CH₃ R3.46 CHF₂ H I-650 C₂H₅ CH₃ R3.46 CHF₂ H I-651 CH₃ CHF₂ R3.46 CHF₂ H I-652 C₂H₅ CHF₂ R3.46 CHF₂ H I-653 CH₃ CF₃ R3.46 CHF₂ H I-654 C₂H₅ CF₃ R3.46 CHF₂ H I-655 CH₃ CH₃ R3.47 CHF₂ H I-656 C₂H₅ CH₃ R3.47 CHF₂ H I-657 CH₃ CHF₂ R3.47 CHF₂ H I-658 C₂H₅ CHF₂ R3.47 CHF₂ H I-659 CH₃ CF₃ R3.47 CHF₂ H I-660 C₂H₅ CF₃ R3.47 CHF₂ H I-661 CH₃ CH₃ R3.48 CHF₂ H I-662 C₂H₅ CH₃ R3.48 CHF₂ H I-663 CH₃ CHF₂ R3.48 CHF₂ H I-664 C₂H₅ CHF₂ R3.48 CHF₂ H I-665 CH₃ CF₃ R3.48 CHF₂ H I-666 C₂H₅ CF₃ R3.48 CHF₂ H I-667 CH₃ CH₃ R3.10 CH₃ H I-668 C₂H₅ CH₃ R3.10 CH₃ H I-669 CH₃ CHF₂ R3.10 CH₃ H I-670 C₂H₅ CHF₂ R3.10 CH₃ H I-671 CH₃ CF₃ R3.10 CH₃ H I-672 C₂H₅ CF₃ R3.10 CH₃ H I-673 CH₃ CH₃ R3.11 CH₃ H I-674 C₂H₅ CH₃ R3.11 CH₃ H I-675 CH₃ CHF₂ R3.11 CH₃ H I-676 C₂H₅ CHF₂ R3.11 CH₃ H I-677 CH₃ CF₃ R3.11 CH₃ H I-678 C₂H₅ CF₃ R3.11 CH₃ H I-679 CH₃ CH₃ R3.12 CH₃ H I-680 C₂H₅ CH₃ R3.12 CH₃ H I-681 CH₃ CHF₂ R3.12 CH₃ H I-682 C₂H₅ CHF₂ R3.12 CH₃ H I-683 CH₃ CF₃ R3.12 CH₃ H I-684 C₂H₅ CF₃ R3.12 CH₃ H I-685 CH₃ CH₃ R3.13 CH₃ H I-686 C₂H₅ CH₃ R3.13 CH₃ H I-687 CH₃ CHF₂ R3.13 CH₃ H I-688 C₂H₅ CHF₂ R3.13 CH₃ H I-689 CH₃ CF₃ R3.13 CH₃ H I-690 C₂H₅ CF₃ R3.13 CH₃ H I-691 CH₃ CH₃ R3.15 CH₃ H I-692 C₂H₅ CH₃ R3.15 CH₃ H I-693 CH₃ CHF₂ R3.15 CH₃ H I-694 C₂H₅ CHF₂ R3.15 CH₃ H I-695 CH₃ CF₃ R3.15 CH₃ H I-696 C₂H₅ CF₃ R3.15 CH₃ H I-697 CH₃ CH₃ R3.16 CH₃ H I-698 C₂H₅ CH₃ R3.16 CH₃ H I-699 CH₃ CHF₂ R3.16 CH₃ H I-700 C₂H₅ CHF₂ R3.16 CH₃ H I-701 CH₃ CF₃ R3.16 CH₃ H I-702 C₂H₅ CF₃ R3.16 CH₃ H I-703 CH₃ CH₃ R3.17 CH₃ H I-704 C₂H₅ CH₃ R3.17 CH₃ H I-705 CH₃ CHF₂ R3.17 CH₃ H I-706 C₂H₅ CHF₂ R3.17 CH₃ H I-707 CH₃ CF₃ R3.17 CH₃ H I-708 C₂H₅ CF₃ R3.17 CH₃ H I-709 CH₃ CH₃ R3.18 CH₃ H I-710 C₂H₅ CH₃ R3.18 CH₃ H I-711 CH₃ CHF₂ R3.18 CH₃ H I-712 C₂H₅ CHF₂ R3.18 CH₃ H I-713 CH₃ CF₃ R3.18 CH₃ H I-714 C₂H₅ CF₃ R3.18 CH₃ H I-715 CH₃ CH₃ R3.19 CH₃ H I-716 C₂H₅ CH₃ R3.19 CH₃ H I-717 CH₃ CHF₂ R3.19 CH₃ H I-718 C₂H₅ CHF₂ R3.19 CH₃ H I-719 CH₃ CF₃ R3.19 CH₃ H I-720 C₂H₅ CF₃ R3.19 CH₃ H I-721 CH₃ CH₃ R3.20 CH₃ H I-722 C₂H₅ CH₃ R3.20 CH₃ H I-723 CH₃ CHF₂ R3.20 CH₃ H I-724 C₂H₅ CHF₂ R3.20 CH₃ H I-725 CH₃ CF₃ R3.20 CH₃ H I-726 C₂H₅ CF₃ R3.20 CH₃ H I-727 CH₃ CH₃ R3.21 CH₃ H I-728 C₂H₅ CH₃ R3.21 CH₃ H I-729 CH₃ CHF₂ R3.21 CH₃ H I-730 C₂H₅ CHF₂ R3.21 CH₃ H I-731 CH₃ CF₃ R3.21 CH₃ H I-732 C₂H₅ CF₃ R3.21 CH₃ H I-733 CH₃ CH₃ R3.22 CH₃ H I-734 C₂H₅ CH₃ R3.22 CH₃ H I-735 CH₃ CHF₂ R3.22 CH₃ H I-736 C₂H₅ CHF₂ R3.22 CH₃ H I-737 CH₃ CF₃ R3.22 CH₃ H I-738 C₂H₅ CF₃ R3.22 CH₃ H I-739 CH₃ CH₃ R3.23 CH₃ H I-740 C₂H₅ CH₃ R3.23 CH₃ H I-741 CH₃ CHF₂ R3.23 CH₃ H I-742 C₂H₅ CHF₂ R3.23 CH₃ H I-743 CH₃ CF₃ R3.23 CH₃ H I-744 C₂H₅ CF₃ R3.23 CH₃ H I-745 CH₃ CH₃ R3.24 CH₃ H I-746 C₂H₅ CH₃ R3.24 CH₃ H I-747 CH₃ CHF₂ R3.24 CH₃ H I-748 C₂H₅ CHF₂ R3.24 CH₃ H I-749 CH₃ CF₃ R3.24 CH₃ H I-750 C₂H₅ CF₃ R3.24 CH₃ H I-751 CH₃ CH₃ R3.25 CH₃ H I-752 C₂H₅ CH₃ R3.25 CH₃ H I-753 CH₃ CHF₂ R3.25 CH₃ H I-754 C₂H₅ CHF₂ R3.25 CH₃ H I-755 CH₃ CF₃ R3.25 CH₃ H I-756 C₂H₅ CF₃ R3.25 CH₃ H I-757 CH₃ CH₃ R3.26 CH₃ H I-758 C₂H₅ CH₃ R3.26 CH₃ H I-759 CH₃ CHF₂ R3.26 CH₃ H I-760 C₂H₅ CHF₂ R3.26 CH₃ H I-761 CH₃ CF₃ R3.26 CH₃ H I-762 C₂H₅ CF₃ R3.26 CH₃ H I-763 CH₃ CH₃ R3.27 CH₃ H I-764 C₂H₅ CH₃ R3.27 CH₃ H I-765 CH₃ CHF₂ R3.27 CH₃ H I-766 C₂H₅ CHF₂ R3.27 CH₃ H I-767 CH₃ CF₃ R3.27 CH₃ H I-768 C₂H₅ CF₃ R3.27 CH₃ H I-769 CH₃ CH₃ R3.28 CH₃ H I-770 C₂H₅ CH₃ R3.28 CH₃ H I-771 CH₃ CHF₂ R3.28 CH₃ H I-772 C₂H₅ CHF₂ R3.28 CH₃ H I-773 CH₃ CF₃ R3.28 CH₃ H I-774 C₂H₅ CF₃ R3.28 CH₃ H I-775 CH₃ CH₃ R3.29 CH₃ H I-776 C₂H₅ CH₃ R3.29 CH₃ H I-777 CH₃ CHF₂ R3.29 CH₃ H I-778 C₂H₅ CHF₂ R3.29 CH₃ H I-779 CH₃ CF₃ R3.29 CH₃ H I-780 C₂H₅ CF₃ R3.29 CH₃ H I-781 CH₃ CH₃ R3.30 CH₃ H I-782 C₂H₅ CH₃ R3.30 CH₃ H I-783 CH₃ CHF₂ R3.30 CH₃ H I-784 C₂H₅ CHF₂ R3.30 CH₃ H I-785 CH₃ CF₃ R3.30 CH₃ H I-786 C₂H₅ CF₃ R3.30 CH₃ H I-787 CH₃ CH₃ R3.31 CH₃ H I-788 C₂H₅ CH₃ R3.31 CH₃ H I-789 CH₃ CHF₂ R3.31 CH₃ H I-790 C₂H₅ CHF₂ R3.31 CH₃ H I-791 CH₃ CF₃ R3.31 CH₃ H I-792 C₂H₅ CF₃ R3.31 CH₃ H I-793 CH₃ CH₃ R3.32 CH₃ H I-794 C₂H₅ CH₃ R3.32 CH₃ H I-795 CH₃ CHF₂ R3.32 CH₃ H I-796 C₂H₅ CHF₂ R3.32 CH₃ H I-797 CH₃ CF₃ R3.32 CH₃ H I-798 C₂H₅ CF₃ R3.32 CH₃ H I-799 CH₃ CH₃ R3.33 CH₃ H I-800 C₂H₅ CH₃ R3.33 CH₃ H I-801 CH₃ CHF₂ R3.33 CH₃ H I-802 C₂H₅ CHF₂ R3.33 CH₃ H I-803 CH₃ CF₃ R3.33 CH₃ H I-804 C₂H₅ CF₃ R3.33 CH₃ H I-805 CH₃ CH₃ R3.34 CH₃ H I-806 C₂H₅ CH₃ R3.34 CH₃ H I-807 CH₃ CHF₂ R3.34 CH₃ H I-808 C₂H₅ CHF₂ R3.34 CH₃ H I-809 CH₃ CF₃ R3.34 CH₃ H I-810 C₂H₅ CF₃ R3.34 CH₃ H I-811 CH₃ CH₃ R3.35 CH₃ H I-812 C₂H₅ CH₃ R3.35 CH₃ H I-813 CH₃ CHF₂ R3.35 CH₃ H I-814 C₂H₅ CHF₂ R3.35 CH₃ H I-815 CH₃ CF₃ R3.35 CH₃ H I-816 C₂H₅ CF₃ R3.35 CH₃ H I-817 CH₃ CH₃ R3.36 CH₃ H I-818 C₂H₅ CH₃ R3.36 CH₃ H I-819 CH₃ CHF₂ R3.36 CH₃ H I-820 C₂H₅ CHF₂ R3.36 CH₃ H I-821 CH₃ CF₃ R3.36 CH₃ H I-822 C₂H₅ CF₃ R3.36 CH₃ H I-823 CH₃ CH₃ R3.37 CH₃ H I-824 C₂H₅ CH₃ R3.37 CH₃ H I-825 CH₃ CHF₂ R3.37 CH₃ H I-826 C₂H₅ CHF₂ R3.37 CH₃ H I-827 CH₃ CF₃ R3.37 CH₃ H I-828 C₂H₅ CF₃ R3.37 CH₃ H I-829 CH₃ CH₃ R3.38 CH₃ H I-830 C₂H₅ CH₃ R3.38 CH₃ H I-831 CH₃ CHF₂ R3.38 CH₃ H I-832 C₂H₅ CHF₂ R3.38 CH₃ H I-833 CH₃ CF₃ R3.38 CH₃ H I-834 C₂H₅ CF₃ R3.38 CH₃ H I-835 CH₃ CH₃ R3.39 CH₃ H I-836 C₂H₅ CH₃ R3.39 CH₃ H I-837 CH₃ CHF₂ R3.39 CH₃ H I-838 C₂H₅ CHF₂ R3.39 CH₃ H I-839 CH₃ CF₃ R3.39 CH₃ H I-840 C₂H₅ CF₃ R3.39 CH₃ H I-841 CH₃ CH₃ R3.40 CH₃ H I-842 C₂H₅ CH₃ R3.40 CH₃ H I-843 CH₃ CHF₂ R3.40 CH₃ H I-844 C₂H₅ CHF₂ R3.40 CH₃ H I-845 CH₃ CF₃ R3.40 CH₃ H I-846 C₂H₅ CF₃ R3.40 CH₃ H I-847 CH₃ CH₃ R3.41 CH₃ H I-848 C₂H₅ CH₃ R3.41 CH₃ H I-849 CH₃ CHF₂ R3.41 CH₃ H I-850 C₂H₅ CHF₂ R3.41 CH₃ H I-851 CH₃ CF₃ R3.41 CH₃ H I-852 C₂H₅ CF₃ R3.41 CH₃ H I-853 CH₃ CH₃ R3.42 CH₃ H I-854 C₂H₅ CH₃ R3.42 CH₃ H I-855 CH₃ CHF₂ R3.42 CH₃ H I-856 C₂H₅ CHF₂ R3.42 CH₃ H I-857 CH₃ CF₃ R3.42 CH₃ H I-858 C₂H₅ CF₃ R3.42 CH₃ H I-859 CH₃ CH₃ R3.43 CH₃ H I-860 C₂H₅ CH₃ R3.43 CH₃ H I-861 CH₃ CHF₂ R3.43 CH₃ H I-862 C₂H₅ CHF₂ R3.43 CH₃ H I-863 CH₃ CF₃ R3.43 CH₃ H I-864 C₂H₅ CF₃ R3.43 CH₃ H I-865 CH₃ CH₃ R3.44 CH₃ H I-866 C₂H₅ CH₃ R3.44 CH₃ H I-867 CH₃ CHF₂ R3.44 CH₃ H I-868 C₂H₅ CHF₂ R3.44 CH₃ H I-869 CH₃ CF₃ R3.44 CH₃ H I-870 C₂H₅ CF₃ R3.44 CH₃ H I-871 CH₃ CH₃ R3.45 CH₃ H I-872 C₂H₅ CH₃ R3.45 CH₃ H I-873 CH₃ CHF₂ R3.45 CH₃ H I-874 C₂H₅ CHF₂ R3.45 CH₃ H I-875 CH₃ CF₃ R3.45 CH₃ H I-876 C₂H₅ CF₃ R3.45 CH₃ H I-877 CH₃ CH₃ R3.46 CH₃ H I-878 C₂H₅ CH₃ R3.46 CH₃ H I-879 CH₃ CHF₂ R3.46 CH₃ H I-880 C₂H₅ CHF₂ R3.46 CH₃ H I-881 CH₃ CF₃ R3.46 CH₃ H I-882 C₂H₅ CF₃ R3.46 CH₃ H I-883 CH₃ CH₃ R3.48 CH₃ H I-884 C₂H₅ CH₃ R3.48 CH₃ H I-885 CH₃ CHF₂ R3.48 CH₃ H I-886 C₂H₅ CHF₂ R3.48 CH₃ H I-887 CH₃ CF₃ R3.48 CH₃ H I-888 C₂H₅ CF₃ R3.48 CH₃ H I-889 CH₃ CH₃ R3.10 C₂H₅ H I-890 C₂H₅ CH₃ R3.10 C₂H₅ H I-891 CH₃ CHF₂ R3.10 C₂H₅ H I-892 C₂H₅ CHF₂ R3.10 C₂H₅ H I-893 CH₃ CF₃ R3.10 C₂H₅ H I-894 C₂H₅ CF₃ R3.10 C₂H₅ H I-895 CH₃ CH₃ R3.11 C₂H₅ H I-896 C₂H₅ CH₃ R3.11 C₂H₅ H I-897 CH₃ CHF₂ R3.11 C₂H₅ H I-898 C₂H₅ CHF₂ R3.11 C₂H₅ H I-899 CH₃ CF₃ R3.11 C₂H₅ H I-900 C₂H₅ CF₃ R3.11 C₂H₅ H I-901 CH₃ CH₃ R3.12 C₂H₅ H I-902 C₂H₅ CH₃ R3.12 C₂H₅ H I-903 CH₃ CHF₂ R3.12 C₂H₅ H I-904 C₂H₅ CHF₂ R3.12 C₂H₅ H I-905 CH₃ CF₃ R3.12 C₂H₅ H I-906 C₂H₅ CF₃ R3.12 C₂H₅ H I-907 CH₃ CH₃ R3.13 C₂H₅ H I-908 C₂H₅ CH₃ R3.13 C₂H₅ H I-909 CH₃ CHF₂ R3.13 C₂H₅ H I-910 C₂H₅ CHF₂ R3.13 C₂H₅ H I-911 CH₃ CF₃ R3.13 C₂H₅ H I-912 C₂H₅ CF₃ R3.13 C₂H₅ H I-913 CH₃ CH₃ R3.14 C₂H₅ H I-914 C₂H₅ CH₃ R3.14 C₂H₅ H I-915 CH₃ CHF₂ R3.14 C₂H₅ H I-916 C₂H₅ CHF₂ R3.14 C₂H₅ H I-917 CH₃ CF₃ R3.14 C₂H₅ H I-918 C₂H₅ CF₃ R3.14 C₂H₅ H I-919 CH₃ CH₃ R3.15 C₂H₅ H I-920 C₂H₅ CH₃ R3.15 C₂H₅ H I-921 CH₃ CHF₂ R3.15 C₂H₅ H I-922 C₂H₅ CHF₂ R3.15 C₂H₅ H I-923 CH₃ CF₃ R3.15 C₂H₅ H I-924 C₂H₅ CF₃ R3.15 C₂H₅ H I-925 CH₃ CH₃ R3.16 C₂H₅ H I-926 C₂H₅ CH₃ R3.16 C₂H₅ H I-927 CH₃ CHF₂ R3.16 C₂H₅ H I-928 C₂H₅ CHF₂ R3.16 C₂H₅ H I-929 CH₃ CF₃ R3.16 C₂H₅ H I-930 C₂H₅ CF₃ R3.16 C₂H₅ H I-931 CH₃ CH₃ R3.17 C₂H₅ H I-932 C₂H₅ CH₃ R3.17 C₂H₅ H I-933 CH₃ CHF₂ R3.17 C₂H₅ H I-934 C₂H₅ CHF₂ R3.17 C₂H₅ H I-935 CH₃ CF₃ R3.17 C₂H₅ H I-936 C₂H₅ CF₃ R3.17 C₂H₅ H I-937 CH₃ CH₃ R3.18 C₂H₅ H I-938 C₂H₅ CH₃ R3.18 C₂H₅ H I-939 CH₃ CHF₂ R3.18 C₂H₅ H I-940 C₂H₅ CHF₂ R3.18 C₂H₅ H I-941 CH₃ CF₃ R3.18 C₂H₅ H I-942 C₂H₅ CF₃ R3.18 C₂H₅ H I-943 CH₃ CH₃ R3.19 C₂H₅ H I-944 C₂H₅ CH₃ R3.19 C₂H₅ H I-945 CH₃ CHF₂ R3.19 C₂H₅ H I-946 C₂H₅ CHF₂ R3.19 C₂H₅ H I-947 CH₃ CF₃ R3.19 C₂H₅ H I-948 C₂H₅ CF₃ R3.19 C₂H₅ H I-949 CH₃ CH₃ R3.20 C₂H₅ H I-950 C₂H₅ CH₃ R3.20 C₂H₅ H I-951 CH₃ CHF₂ R3.20 C₂H₅ H I-952 C₂H₅ CHF₂ R3.20 C₂H₅ H I-953 CH₃ CF₃ R3.20 C₂H₅ H I-954 C₂H₅ CF₃ R3.20 C₂H₅ H I-955 CH₃ CH₃ R3.21 C₂H₅ H I-956 C₂H₅ CH₃ R3.21 C₂H₅ H I-957 CH₃ CHF₂ R3.21 C₂H₅ H I-958 C₂H₅ CHF₂ R3.21 C₂H₅ H I-959 CH₃ CF₃ R3.21 C₂H₅ H I-960 C₂H₅ CF₃ R3.21 C₂H₅ H I-961 CH₃ CH₃ R3.22 C₂H₅ H I-962 C₂H₅ CH₃ R3.22 C₂H₅ H I-963 CH₃ CHF₂ R3.22 C₂H₅ H I-964 C₂H₅ CHF₂ R3.22 C₂H₅ H I-965 CH₃ CF₃ R3.22 C₂H₅ H I-966 C₂H₅ CF₃ R3.22 C₂H₅ H I-967 CH₃ CH₃ R3.23 C₂H₅ H I-968 C₂H₅ CH₃ R3.23 C₂H₅ H I-969 CH₃ CHF₂ R3.23 C₂H₅ H I-970 C₂H₅ CHF₂ R3.23 C₂H₅ H I-971 CH₃ CF₃ R3.23 C₂H₅ H I-972 C₂H₅ CF₃ R3.23 C₂H₅ H I-973 CH₃ CH₃ R3.24 C₂H₅ H I-974 C₂H₅ CH₃ R3.24 C₂H₅ H I-975 CH₃ CHF₂ R3.24 C₂H₅ H I-976 C₂H₅ CHF₂ R3.24 C₂H₅ H I-977 CH₃ CF₃ R3.24 C₂H₅ H I-978 C₂H₅ CF₃ R3.24 C₂H₅ H I-979 CH₃ CH₃ R3.25 C₂H₅ H I-980 C₂H₅ CH₃ R3.25 C₂H₅ H I-981 CH₃ CHF₂ R3.25 C₂H₅ H I-982 C₂H₅ CHF₂ R3.25 C₂H₅ H I-983 CH₃ CF₃ R3.25 C₂H₅ H I-984 C₂H₅ CF₃ R3.25 C₂H₅ H I-985 CH₃ CH₃ R3.26 C₂H₅ H I-986 C₂H₅ CH₃ R3.26 C₂H₅ H I-987 CH₃ CHF₂ R3.26 C₂H₅ H I-988 C₂H₅ CHF₂ R3.26 C₂H₅ H I-989 CH₃ CF₃ R3.26 C₂H₅ H I-990 C₂H₅ CF₃ R3.26 C₂H₅ H I-991 CH₃ CH₃ R3.27 C₂H₅ H I-992 C₂H₅ CH₃ R3.27 C₂H₅ H I-993 CH₃ CHF₂ R3.27 C₂H₅ H I-994 C₂H₅ CHF₂ R3.27 C₂H₅ H I-995 CH₃ CF₃ R3.27 C₂H₅ H I-996 C₂H₅ CF₃ R3.27 C₂H₅ H I-997 CH₃ CH₃ R3.28 C₂H₅ H I-998 C₂H₅ CH₃ R3.28 C₂H₅ H I-999 CH₃ CHF₂ R3.28 C₂H₅ H I-1000 C₂H₅ CHF₂ R3.28 C₂H₅ H I-1001 CH₃ CF₃ R3.28 C₂H₅ H I-1002 C₂H₅ CF₃ R3.28 C₂H₅ H I-1003 CH₃ CH₃ R3.29 C₂H₅ H I-1004 C₂H₅ CH₃ R3.29 C₂H₅ H I-1005 CH₃ CHF₂ R3.29 C₂H₅ H I-1006 C₂H₅ CHF₂ R3.29 C₂H₅ H I-1007 CH₃ CF₃ R3.29 C₂H₅ H I-1008 C₂H₅ CF₃ R3.29 C₂H₅ H I-1009 CH₃ CH₃ R3.30 C₂H₅ H I-1010 C₂H₅ CH₃ R3.30 C₂H₅ H I-1011 CH₃ CHF₂ R3.30 C₂H₅ H I-1012 C₂H₅ CHF₂ R3.30 C₂H₅ H I-1013 CH₃ CF₃ R3.30 C₂H₅ H I-1014 C₂H₅ CF₃ R3.30 C₂H₅ H I-1015 CH₃ CH₃ R3.31 C₂H₅ H I-1016 C₂H₅ CH₃ R3.31 C₂H₅ H I-1017 CH₃ CHF₂ R3.31 C₂H₅ H I-1018 C₂H₅ CHF₂ R3.31 C₂H₅ H I-1019 CH₃ CF₃ R3.31 C₂H₅ H I-1020 C₂H₅ CF₃ R3.31 C₂H₅ H I-1021 CH₃ CH₃ R3.32 C₂H₅ H I-1022 C₂H₅ CH₃ R3.32 C₂H₅ H I-1023 CH₃ CHF₂ R3.32 C₂H₅ H I-1024 C₂H₅ CHF₂ R3.32 C₂H₅ H I-1025 CH₃ CF₃ R3.32 C₂H₅ H I-1026 C₂H₅ CF₃ R3.32 C₂H₅ H I-1027 CH₃ CH₃ R3.33 C₂H₅ H I-1028 C₂H₅ CH₃ R3.33 C₂H₅ H I-1029 CH₃ CHF₂ R3.33 C₂H₅ H I-1030 C₂H₅ CHF₂ R3.33 C₂H₅ H I-1031 CH₃ CF₃ R3.33 C₂H₅ H I-1032 C₂H₅ CF₃ R3.33 C₂H₅ H I-1033 CH₃ CH₃ R3.34 C₂H₅ H I-1034 C₂H₅ CH₃ R3.34 C₂H₅ H I-1035 CH₃ CHF₂ R3.34 C₂H₅ H I-1036 C₂H₅ CHF₂ R3.34 C₂H₅ H I-1037 CH₃ CF₃ R3.34 C₂H₅ H I-1038 C₂H₅ CF₃ R3.34 C₂H₅ H I-1039 CH₃ CH₃ R3.35 C₂H₅ H I-1040 C₂H₅ CH₃ R3.35 C₂H₅ H I-1041 CH₃ CHF₂ R3.35 C₂H₅ H I-1042 C₂H₅ CHF₂ R3.35 C₂H₅ H I-1043 CH₃ CF₃ R3.35 C₂H₅ H I-1044 C₂H₅ CF₃ R3.35 C₂H₅ H I-1045 CH₃ CH₃ R3.36 C₂H₅ H I-1046 C₂H₅ CH₃ R3.36 C₂H₅ H I-1047 CH₃ CHF₂ R3.36 C₂H₅ H I-1048 C₂H₅ CHF₂ R3.36 C₂H₅ H I-1049 CH₃ CF₃ R3.36 C₂H₅ H I-1050 C₂H₅ CF₃ R3.36 C₂H₅ H I-1051 CH₃ CH₃ R3.37 C₂H₅ H I-1052 C₂H₅ CH₃ R3.37 C₂H₅ H I-1053 CH₃ CHF₂ R3.37 C₂H₅ H I-1054 C₂H₅ CHF₂ R3.37 C₂H₅ H I-1055 CH₃ CF₃ R3.37 C₂H₅ H I-1056 C₂H₅ CF₃ R3.37 C₂H₅ H I-1057 CH₃ CH₃ R3.38 C₂H₅ H I-1058 C₂H₅ CH₃ R3.38 C₂H₅ H I-1059 CH₃ CHF₂ R3.38 C₂H₅ H I-1060 C₂H₅ CHF₂ R3.38 C₂H₅ H I-1061 CH₃ CF₃ R3.38 C₂H₅ H I-1062 C₂H₅ CF₃ R3.38 C₂H₅ H I-1063 CH₃ CH₃ R3.39 C₂H₅ H I-1064 C₂H₅ CH₃ R3.39 C₂H₅ H I-1065 CH₃ CHF₂ R3.39 C₂H₅ H I-1066 C₂H₅ CHF₂ R3.39 C₂H₅ H I-1067 CH₃ CF₃ R3.39 C₂H₅ H I-1068 C₂H₅ CF₃ R3.39 C₂H₅ H I-1069 CH₃ CH₃ R3.40 C₂H₅ H I-1070 C₂H₅ CH₃ R3.40 C₂H₅ H I-1071 CH₃ CHF₂ R3.40 C₂H₅ H I-1072 C₂H₅ CHF₂ R3.40 C₂H₅ H I-1073 CH₃ CF₃ R3.40 C₂H₅ H I-1074 C₂H₅ CF₃ R3.40 C₂H₅ H I-1075 CH₃ CH₃ R3.41 C₂H₅ H I-1076 C₂H₅ CH₃ R3.41 C₂H₅ H I-1077 CH₃ CHF₂ R3.41 C₂H₅ H I-1078 C₂H₅ CHF₂ R3.41 C₂H₅ H I-1079 CH₃ CF₃ R3.41 C₂H₅ H I-1080 C₂H₅ CF₃ R3.41 C₂H₅ H I-1081 CH₃ CH₃ R3.42 C₂H₅ H I-1082 C₂H₅ CH₃ R3.42 C₂H₅ H I-1083 CH₃ CHF₂ R3.42 C₂H₅ H I-1084 C₂H₅ CHF₂ R3.42 C₂H₅ H I-1085 CH₃ CF₃ R3.42 C₂H₅ H I-1086 C₂H₅ CF₃ R3.42 C₂H₅ H I-1087 CH₃ CH₃ R3.43 C₂H₅ H I-1088 C₂H₅ CH₃ R3.43 C₂H₅ H I-1089 CH₃ CHF₂ R3.43 C₂H₅ H I-1090 C₂H₅ CHF₂ R3.43 C₂H₅ H I-1091 CH₃ CF₃ R3.43 C₂H₅ H I-1092 C₂H₅ CF₃ R3.43 C₂H₅ H I-1093 CH₃ CH₃ R3.44 C₂H₅ H I-1094 C₂H₅ CH₃ R3.44 C₂H₅ H I-1095 CH₃ CHF₂ R3.44 C₂H₅ H I-1096 C₂H₅ CHF₂ R3.44 C₂H₅ H I-1097 CH₃ CF₃ R3.44 C₂H₅ H I-1098 C₂H₅ CF₃ R3.44 C₂H₅ H I-1099 CH₃ CH₃ R3.45 C₂H₅ H I-1100 C₂H₅ CH₃ R3.45 C₂H₅ H I-1101 CH₃ CHF₂ R3.45 C₂H₅ H I-1102 C₂H₅ CHF₂ R3.45 C₂H₅ H I-1103 CH₃ CF₃ R3.45 C₂H₅ H I-1104 C₂H₅ CF₃ R3.45 C₂H₅ H I-1105 CH₃ CH₃ R3.46 C₂H₅ H I-1106 C₂H₅ CH₃ R3.46 C₂H₅ H I-1107 CH₃ CHF₂ R3.46 C₂H₅ H I-1108 C₂H₅ CHF₂ R3.46 C₂H₅ H I-1109 CH₃ CF₃ R3.46 C₂H₅ H I-1110 C₂H₅ CF₃ R3.46 C₂H₅ H I-1111 CH₃ CH₃ R3.47 C₂H₅ H I-1112 C₂H₅ CH₃ R3.47 C₂H₅ H I-1113 CH₃ CHF₂ R3.47 C₂H₅ H I-1114 C₂H₅ CHF₂ R3.47 C₂H₅ H I-1115 CH₃ CF₃ R3.47 C₂H₅ H I-1116 C₂H₅ CF₃ R3.47 C₂H₅ H I-1117 CH₃ CH₃ R3.48 C₂H₅ H I-1118 C₂H₅ CH₃ R3.48 C₂H₅ H I-1119 CH₃ CHF₂ R3.48 C₂H₅ H I-1120 C₂H₅ CHF₂ R3.48 C₂H₅ H I-1121 CH₃ CF₃ R3.48 C₂H₅ H I-1122 C₂H₅ CF₃ R3.48 C₂H₅ H I-1123 CH₃ CH₃ R3.10 CF₃ H I-1124 C₂H₅ CH₃ R3.10 CF₃ H I-1125 CH₃ CHF₂ R3.10 CF₃ H I-1126 C₂H₅ CHF₂ R3.10 CF₃ H I-1127 CH₃ CF₃ R3.10 CF₃ H I-1128 C₂H₅ CF₃ R3.10 CF₃ H I-1129 CH₃ CH₃ R3.11 CF₃ H I-1130 C₂H₅ CH₃ R3.11 CF₃ H I-1131 CH₃ CHF₂ R3.11 CF₃ H I-1132 C₂H₅ CHF₂ R3.11 CF₃ H I-1133 CH₃ CF₃ R3.11 CF₃ H I-1134 C₂H₅ CF₃ R3.11 CF₃ H I-1135 CH₃ CH₃ R3.12 CF₃ H I-1136 C₂H₅ CH₃ R3.12 CF₃ H I-1137 CH₃ CHF₂ R3.12 CF₃ H I-1138 C₂H₅ CHF₂ R3.12 CF₃ H I-1139 CH₃ CF₃ R3.12 CF₃ H I-1140 C₂H₅ CF₃ R3.12 CF₃ H I-1141 CH₃ CH₃ R3.13 CF₃ H I-1142 C₂H₅ CH₃ R3.13 CF₃ H I-1143 CH₃ CHF₂ R3.13 CF₃ H I-1144 C₂H₅ CHF₂ R3.13 CF₃ H I-1145 CH₃ CF₃ R3.13 CF₃ H I-1146 C₂H₅ CF₃ R3.13 CF₃ H I-1147 CH₃ CH₃ R3.14 CF₃ H I-1148 C₂H₅ CH₃ R3.14 CF₃ H I-1149 CH₃ CHF₂ R3.14 CF₃ H I-1150 C₂H₅ CHF₂ R3.14 CF₃ H I-1151 CH₃ CF₃ R3.14 CF₃ H I-1152 C₂H₅ CF₃ R3.14 CF₃ H I-1153 CH₃ CH₃ R3.15 CF₃ H I-1154 C₂H₅ CH₃ R3.15 CF₃ H I-1155 CH₃ CHF₂ R3.15 CF₃ H I-1156 C₂H₅ CHF₂ R3.15 CF₃ H I-1157 CH₃ CF₃ R3.15 CF₃ H I-1158 C₂H₅ CF₃ R3.15 CF₃ H I-1159 CH₃ CH₃ R3.16 CF₃ H I-1160 C₂H₅ CH₃ R3.16 CF₃ H I-1161 CH₃ CHF₂ R3.16 CF₃ H I-1162 C₂H₅ CHF₂ R3.16 CF₃ H I-1163 CH₃ CF₃ R3.16 CF₃ H I-1164 C₂H₅ CF₃ R3.16 CF₃ H I-1165 CH₃ CH₃ R3.17 CF₃ H I-1166 C₂H₅ CH₃ R3.17 CF₃ H I-1167 CH₃ CHF₂ R3.17 CF₃ H I-1168 C₂H₅ CHF₂ R3.17 CF₃ H I-1169 CH₃ CF₃ R3.17 CF₃ H I-1170 C₂H₅ CF₃ R3.17 CF₃ H I-1171 CH₃ CH₃ R3.18 CF₃ H I-1172 C₂H₅ CH₃ R3.18 CF₃ H I-1173 CH₃ CHF₂ R3.18 CF₃ H I-1174 C₂H₅ CHF₂ R3.18 CF₃ H I-1175 CH₃ CF₃ R3.18 CF₃ H I-1176 C₂H₅ CF₃ R3.18 CF₃ H I-1177 CH₃ CH₃ R3.19 CF₃ H I-1178 C₂H₅ CH₃ R3.19 CF₃ H I-1179 CH₃ CHF₂ R3.19 CF₃ H I-1180 C₂H₅ CHF₂ R3.19 CF₃ H I-1181 CH₃ CF₃ R3.19 CF₃ H I-1182 C₂H₅ CF₃ R3.19 CF₃ H I-1183 CH₃ CH₃ R3.20 CF₃ H I-1184 C₂H₅ CH₃ R3.20 CF₃ H I-1185 CH₃ CHF₂ R3.20 CF₃ H I-1186 C₂H₅ CHF₂ R3.20 CF₃ H I-1187 CH₃ CF₃ R3.20 CF₃ H I-1188 C₂H₅ CF₃ R3.20 CF₃ H I-1189 CH₃ CH₃ R3.21 CF₃ H I-1190 C₂H₅ CH₃ R3.21 CF₃ H I-1191 CH₃ CHF₂ R3.21 CF₃ H I-1192 C₂H₅ CHF₂ R3.21 CF₃ H I-1193 CH₃ CF₃ R3.21 CF₃ H I-1194 C₂H₅ CF₃ R3.21 CF₃ H I-1195 CH₃ CH₃ R3.22 CF₃ H I-1196 C₂H₅ CH₃ R3.22 CF₃ H I-1197 CH₃ CHF₂ R3.22 CF₃ H I-1198 C₂H₅ CHF₂ R3.22 CF₃ H I-1199 CH₃ CF₃ R3.22 CF₃ H I-1200 C₂H₅ CF₃ R3.22 CF₃ H I-1201 CH₃ CH₃ R3.23 CF₃ H I-1202 C₂H₅ CH₃ R3.23 CF₃ H I-1203 CH₃ CHF₂ R3.23 CF₃ H I-1204 C₂H₅ CHF₂ R3.23 CF₃ H I-1205 CH₃ CF₃ R3.23 CF₃ H I-1206 C₂H₅ CF₃ R3.23 CF₃ H I-1207 CH₃ CH₃ R3.24 CF₃ H I-1208 C₂H₅ CH₃ R3.24 CF₃ H I-1209 CH₃ CHF₂ R3.24 CF₃ H I-1210 C₂H₅ CHF₂ R3.24 CF₃ H I-1211 CH₃ CF₃ R3.24 CF₃ H I-1212 C₂H₅ CF₃ R3.24 CF₃ H I-1213 CH₃ CH₃ R3.25 CF₃ H I-1214 C₂H₅ CH₃ R3.25 CF₃ H I-1215 CH₃ CHF₂ R3.25 CF₃ H I-1216 C₂H₅ CHF₂ R3.25 CF₃ H I-1217 CH₃ CF₃ R3.25 CF₃ H I-1218 C₂H₅ CF₃ R3.25 CF₃ H I-1219 CH₃ CH₃ R3.26 CF₃ H I-1220 C₂H₅ CH₃ R3.26 CF₃ H I-1221 CH₃ CHF₂ R3.26 CF₃ H I-1222 C₂H₅ CHF₂ R3.26 CF₃ H I-1223 CH₃ CF₃ R3.26 CF₃ H I-1224 C₂H₅ CF₃ R3.26 CF₃ H I-1225 CH₃ CH₃ R3.27 CF₃ H I-1226 C₂H₅ CH₃ R3.27 CF₃ H I-1227 CH₃ CHF₂ R3.27 CF₃ H I-1228 C₂H₅ CHF₂ R3.27 CF₃ H I-1229 CH₃ CF₃ R3.27 CF₃ H I-1230 C₂H₅ CF₃ R3.27 CF₃ H I-1231 CH₃ CH₃ R3.28 CF₃ H I-1232 C₂H₅ CH₃ R3.28 CF₃ H I-1233 CH₃ CHF₂ R3.28 CF₃ H I-1234 C₂H₅ CHF₂ R3.28 CF₃ H I-1235 CH₃ CF₃ R3.28 CF₃ H I-1236 C₂H₅ CF₃ R3.28 CF₃ H I-1237 CH₃ CH₃ R3.29 CF₃ H I-1238 C₂H₅ CH₃ R3.29 CF₃ H I-1239 CH₃ CHF₂ R3.29 CF₃ H I-1240 C₂H₅ CHF₂ R3.29 CF₃ H I-1241 CH₃ CF₃ R3.29 CF₃ H I-1242 C₂H₅ CF₃ R3.29 CF₃ H I-1243 CH₃ CH₃ R3.30 CF₃ H I-1244 C₂H₅ CH₃ R3.30 CF₃ H I-1245 CH₃ CHF₂ R3.30 CF₃ H I-1246 C₂H₅ CHF₂ R3.30 CF₃ H I-1247 CH₃ CF₃ R3.30 CF₃ H I-1248 C₂H₅ CF₃ R3.30 CF₃ H I-1249 CH₃ CH₃ R3.31 CF₃ H I-1250 C₂H₅ CH₃ R3.31 CF₃ H I-1251 CH₃ CHF₂ R3.31 CF₃ H I-1252 C₂H₅ CHF₂ R3.31 CF₃ H I-1253 CH₃ CF₃ R3.31 CF₃ H I-1254 C₂H₅ CF₃ R3.31 CF₃ H I-1255 CH₃ CH₃ R3.32 CF₃ H I-1256 C₂H₅ CH₃ R3.32 CF₃ H I-1257 CH₃ CHF₂ R3.32 CF₃ H I-1258 C₂H₅ CHF₂ R3.32 CF₃ H I-1259 CH₃ CF₃ R3.32 CF₃ H I-1260 C₂H₅ CF₃ R3.32 CF₃ H I-1261 CH₃ CH₃ R3.33 CF₃ H I-1262 C₂H₅ CH₃ R3.33 CF₃ H I-1263 CH₃ CHF₂ R3.33 CF₃ H I-1264 C₂H₅ CHF₂ R3.33 CF₃ H I-1265 CH₃ CF₃ R3.33 CF₃ H I-1266 C₂H₅ CF₃ R3.33 CF₃ H I-1267 CH₃ CH₃ R3.34 CF₃ H I-1268 C₂H₅ CH₃ R3.34 CF₃ H I-1269 CH₃ CHF₂ R3.34 CF₃ H I-1270 C₂H₅ CHF₂ R3.34 CF₃ H I-1271 CH₃ CF₃ R3.34 CF₃ H I-1272 C₂H₅ CF₃ R3.34 CF₃ H I-1273 CH₃ CH₃ R3.35 CF₃ H I-1274 C₂H₅ CH₃ R3.35 CF₃ H I-1275 CH₃ CHF₂ R3.35 CF₃ H I-1276 C₂H₅ CHF₂ R3.35 CF₃ H I-1277 CH₃ CF₃ R3.35 CF₃ H I-1278 C₂H₅ CF₃ R3.35 CF₃ H I-1279 CH₃ CH₃ R3.36 CF₃ H I-1280 C₂H₅ CH₃ R3.36 CF₃ H I-1281 CH₃ CHF₂ R3.36 CF₃ H I-1282 C₂H₅ CHF₂ R3.36 CF₃ H I-1283 CH₃ CF₃ R3.36 CF₃ H I-1284 C₂H₅ CF₃ R3.36 CF₃ H I-1285 CH₃ CH₃ R3.37 CF₃ H I-1286 C₂H₅ CH₃ R3.37 CF₃ H I-1287 CH₃ CHF₂ R3.37 CF₃ H I-1288 C₂H₅ CHF₂ R3.37 CF₃ H I-1289 CH₃ CF₃ R3.37 CF₃ H I-1290 C₂H₅ CF₃ R3.37 CF₃ H I-1291 CH₃ CH₃ R3.38 CF₃ H I-1292 C₂H₅ CH₃ R3.38 CF₃ H I-1293 CH₃ CHF₂ R3.38 CF₃ H I-1294 C₂H₅ CHF₂ R3.38 CF₃ H I-1295 CH₃ CF₃ R3.38 CF₃ H I-1296 C₂H₅ CF₃ R3.38 CF₃ H I-1297 CH₃ CH₃ R3.39 CF₃ H I-1298 C₂H₅ CH₃ R3.39 CF₃ H I-1299 CH₃ CHF₂ R3.39 CF₃ H I-1300 C₂H₅ CHF₂ R3.39 CF₃ H I-1301 CH₃ CF₃ R3.39 CF₃ H I-1302 C₂H₅ CF₃ R3.39 CF₃ H I-1303 CH₃ CH₃ R3.40 CF₃ H I-1304 C₂H₅ CH₃ R3.40 CF₃ H I-1305 CH₃ CHF₂ R3.40 CF₃ H I-1306 C₂H₅ CHF₂ R3.40 CF₃ H I-1307 CH₃ CF₃ R3.40 CF₃ H I-1308 C₂H₅ CF₃ R3.40 CF₃ H I-1309 CH₃ CH₃ R3.41 CF₃ H I-1310 C₂H₅ CH₃ R3.41 CF₃ H I-1311 CH₃ CHF₂ R3.41 CF₃ H I-1312 C₂H₅ CHF₂ R3.41 CF₃ H I-1313 CH₃ CF₃ R3.41 CF₃ H I-1314 C₂H₅ CF₃ R3.41 CF₃ H I-1315 CH₃ CH₃ R3.42 CF₃ H I-1316 C₂H₅ CH₃ R3.42 CF₃ H I-1317 CH₃ CHF₂ R3.42 CF₃ H I-1318 C₂H₅ CHF₂ R3.42 CF₃ H I-1319 CH₃ CF₃ R3.42 CF₃ H I-1320 C₂H₅ CF₃ R3.42 CF₃ H I-1321 CH₃ CH₃ R3.43 CF₃ H I-1322 C₂H₅ CH₃ R3.43 CF₃ H I-1323 CH₃ CHF₂ R3.43 CF₃ H I-1324 C₂H₅ CHF₂ R3.43 CF₃ H I-1325 CH₃ CF₃ R3.43 CF₃ H I-1326 C₂H₅ CF₃ R3.43 CF₃ H I-1327 CH₃ CH₃ R3.44 CF₃ H I-1328 C₂H₅ CH₃ R3.44 CF₃ H I-1329 CH₃ CHF₂ R3.44 CF₃ H I-1330 C₂H₅ CHF₂ R3.44 CF₃ H I-1331 CH₃ CF₃ R3.44 CF₃ H I-1332 C₂H₅ CF₃ R3.44 CF₃ H I-1333 CH₃ CH₃ R3.45 CF₃ H I-1334 C₂H₅ CH₃ R3.45 CF₃ H I-1335 CH₃ CHF₂ R3.45 CF₃ H I-1336 C₂H₅ CHF₂ R3.45 CF₃ H I-1337 CH₃ CF₃ R3.45 CF₃ H I-1338 C₂H₅ CF₃ R3.45 CF₃ H I-1339 CH₃ CH₃ R3.46 CF₃ H I-1340 C₂H₅ CH₃ R3.46 CF₃ H I-1341 CH₃ CHF₂ R3.46 CF₃ H I-1342 C₂H₅ CHF₂ R3.46 CF₃ H I-1343 CH₃ CF₃ R3.46 CF₃ H I-1344 C₂H₅ CF₃ R3.46 CF₃ H I-1345 CH₃ CH₃ R3.47 CF₃ H I-1346 C₂H₅ CH₃ R3.47 CF₃ H I-1347 CH₃ CHF₂ R3.47 CF₃ H I-1348 C₂H₅ CHF₂ R3.47 CF₃ H I-1349 CH₃ CF₃ R3.47 CF₃ H I-1350 C₂H₅ CF₃ R3.47 CF₃ H I-1351 CH₃ CH₃ R3.48 CF₃ H I-1352 C₂H₅ CH₃ R3.48 CF₃ H I-1353 CH₃ CHF₂ R3.48 CF₃ H I-1354 C₂H₅ CHF₂ R3.48 CF₃ H I-1355 CH₃ CF₃ R3.48 CF₃ H I-1356 C₂H₅ CF₃ R3.48 CF₃ H I-1357 CH₃ CH₃ R3.10 CHF₂ CH₃ I-1358 C₂H₅ CH₃ R3.10 CHF₂ CH₃ I-1359 CH₃ CHF₂ R3.10 CHF₂ CH₃ I-1360 C₂H₅ CHF₂ R3.10 CHF₂ CH₃ I-1361 CH₃ CF₃ R3.10 CHF₂ CH₃ I-1362 C₂H₅ CF₃ R3.10 CHF₂ CH₃ I-1363 CH₃ CH₃ R3.11 CHF₂ CH₃ I-1364 C₂H₅ CH₃ R3.11 CHF₂ CH₃ I-1365 CH₃ CHF₂ R3.11 CHF₂ CH₃ I-1366 C₂H₅ CHF₂ R3.11 CHF₂ CH₃ I-1367 CH₃ CF₃ R3.11 CHF₂ CH₃ I-1368 C₂H₅ CF₃ R3.11 CHF₂ CH₃ I-1369 CH₃ CH₃ R3.12 CHF₂ CH₃ I-1370 C₂H₅ CH₃ R3.12 CHF₂ CH₃ I-1371 CH₃ CHF₂ R3.12 CHF₂ CH₃ I-1372 C₂H₅ CHF₂ R3.12 CHF₂ CH₃ I-1373 CH₃ CF₃ R3.12 CHF₂ CH₃ I-1374 C₂H₅ CF₃ R3.12 CHF₂ CH₃ I-1375 CH₃ CH₃ R3.13 CHF₂ CH₃ I-1376 C₂H₅ CH₃ R3.13 CHF₂ CH₃ I-1377 CH₃ CHF₂ R3.13 CHF₂ CH₃ I-1378 C₂H₅ CHF₂ R3.13 CHF₂ CH₃ I-1379 CH₃ CF₃ R3.13 CHF₂ CH₃ I-1380 C₂H₅ CF₃ R3.13 CHF₂ CH₃ I-1381 CH₃ CH₃ R3.14 CHF₂ CH₃ I-1382 C₂H₅ CH₃ R3.14 CHF₂ CH₃ I-1383 CH₃ CHF₂ R3.14 CHF₂ CH₃ I-1384 C₂H₅ CHF₂ R3.14 CHF₂ CH₃ I-1385 CH₃ CF₃ R3.14 CHF₂ CH₃ I-1386 C₂H₅ CF₃ R3.14 CHF₂ CH₃ I-1387 CH₃ CH₃ R3.15 CHF₂ CH₃ I-1388 C₂H₅ CH₃ R3.15 CHF₂ CH₃ I-1389 CH₃ CHF₂ R3.15 CHF₂ CH₃ I-1390 C₂H₅ CHF₂ R3.15 CHF₂ CH₃ I-1391 CH₃ CF₃ R3.15 CHF₂ CH₃ I-1392 C₂H₅ CF₃ R3.15 CHF₂ CH₃ I-1393 CH₃ CH₃ R3.16 CHF₂ CH₃ I-1394 C₂H₅ CH₃ R3.16 CHF₂ CH₃ I-1395 CH₃ CHF₂ R3.16 CHF₂ CH₃ I-1396 C₂H₅ CHF₂ R3.16 CHF₂ CH₃ I-1397 CH₃ CF₃ R3.16 CHF₂ CH₃ I-1398 C₂H₅ CF₃ R3.16 CHF₂ CH₃ I-1399 CH₃ CH₃ R3.17 CHF₂ CH₃ I-1400 C₂H₅ CH₃ R3.17 CHF₂ CH₃ I-1401 CH₃ CHF₂ R3.17 CHF₂ CH₃ I-1402 C₂H₅ CHF₂ R3.17 CHF₂ CH₃ I-1403 CH₃ CF₃ R3.17 CHF₂ CH₃ I-1404 C₂H₅ CF₃ R3.17 CHF₂ CH₃ I-1405 CH₃ CH₃ R3.18 CHF₂ CH₃ I-1406 C₂H₅ CH₃ R3.18 CHF₂ CH₃ I-1407 CH₃ CHF₂ R3.18 CHF₂ CH₃ I-1408 C₂H₅ CHF₂ R3.18 CHF₂ CH₃ I-1409 CH₃ CF₃ R3.18 CHF₂ CH₃ I-1410 C₂H₅ CF₃ R3.18 CHF₂ CH₃ I-1411 CH₃ CH₃ R3.19 CHF₂ CH₃ I-1412 C₂H₅ CH₃ R3.19 CHF₂ CH₃ I-1413 CH₃ CHF₂ R3.19 CHF₂ CH₃ I-1414 C₂H₅ CHF₂ R3.19 CHF₂ CH₃ I-1415 CH₃ CF₃ R3.19 CHF₂ CH₃ I-1416 C₂H₅ CF₃ R3.19 CHF₂ CH₃ I-1417 CH₃ CH₃ R3.20 CHF₂ CH₃ I-1418 C₂H₅ CH₃ R3.20 CHF₂ CH₃ I-1419 CH₃ CHF₂ R3.20 CHF₂ CH₃ I-1420 C₂H₅ CHF₂ R3.20 CHF₂ CH₃ I-1421 CH₃ CF₃ R3.20 CHF₂ CH₃ I-1422 C₂H₅ CF₃ R3.20 CHF₂ CH₃ I-1423 CH₃ CH₃ R3.21 CHF₂ CH₃ I-1424 C₂H₅ CH₃ R3.21 CHF₂ CH₃ I-1425 CH₃ CHF₂ R3.21 CHF₂ CH₃ I-1426 C₂H₅ CHF₂ R3.21 CHF₂ CH₃ I-1427 CH₃ CF₃ R3.21 CHF₂ CH₃ I-1428 C₂H₅ CF₃ R3.21 CHF₂ CH₃ I-1429 CH₃ CH₃ R3.22 CHF₂ CH₃ I-1430 C₂H₅ CH₃ R3.22 CHF₂ CH₃ I-1431 CH₃ CHF₂ R3.22 CHF₂ CH₃ I-1432 C₂H₅ CHF₂ R3.22 CHF₂ CH₃ I-1433 CH₃ CF₃ R3.22 CHF₂ CH₃ I-1434 C₂H₅ CF₃ R3.22 CHF₂ CH₃ I-1435 CH₃ CH₃ R3.23 CHF₂ CH₃ I-1436 C₂H₅ CH₃ R3.23 CHF₂ CH₃ I-1437 CH₃ CHF₂ R3.23 CHF₂ CH₃ I-1438 C₂H₅ CHF₂ R3.23 CHF₂ CH₃ I-1439 CH₃ CF₃ R3.23 CHF₂ CH₃ I-1440 C₂H₅ CF₃ R3.23 CHF₂ CH₃ I-1441 CH₃ CH₃ R3.24 CHF₂ CH₃ I-1442 C₂H₅ CH₃ R3.24 CHF₂ CH₃ I-1443 CH₃ CHF₂ R3.24 CHF₂ CH₃ I-1444 C₂H₅ CHF₂ R3.24 CHF₂ CH₃ I-1445 CH₃ CF₃ R3.24 CHF₂ CH₃ I-1446 C₂H₅ CF₃ R3.24 CHF₂ CH₃ I-1447 CH₃ CH₃ R3.25 CHF₂ CH₃ I-1448 C₂H₅ CH₃ R3.25 CHF₂ CH₃ I-1449 CH₃ CHF₂ R3.25 CHF₂ CH₃ I-1450 C₂H₅ CHF₂ R3.25 CHF₂ CH₃ I-1451 CH₃ CF₃ R3.25 CHF₂ CH₃ I-1452 C₂H₅ CF₃ R3.25 CHF₂ CH₃ I-1453 CH₃ CH₃ R3.26 CHF₂ CH₃ I-1454 C₂H₅ CH₃ R3.26 CHF₂ CH₃ I-1455 CH₃ CHF₂ R3.26 CHF₂ CH₃ I-1456 C₂H₅ CHF₂ R3.26 CHF₂ CH₃ I-1457 CH₃ CF₃ R3.26 CHF₂ CH₃ I-1458 C₂H₅ CF₃ R3.26 CHF₂ CH₃ I-1459 CH₃ CH₃ R3.27 CHF₂ CH₃ I-1460 C₂H₅ CH₃ R3.27 CHF₂ CH₃ I-1461 CH₃ CHF₂ R3.27 CHF₂ CH₃ I-1462 C₂H₅ CHF₂ R3.27 CHF₂ CH₃ I-1463 CH₃ CF₃ R3.27 CHF₂ CH₃ I-1464 C₂H₅ CF₃ R3.27 CHF₂ CH₃ I-1465 CH₃ CH₃ R3.28 CHF₂ CH₃ I-1466 C₂H₅ CH₃ R3.28 CHF₂ CH₃ I-1467 CH₃ CHF₂ R3.28 CHF₂ CH₃ I-1468 C₂H₅ CHF₂ R3.28 CHF₂ CH₃ I-1469 CH₃ CF₃ R3.28 CHF₂ CH₃ I-1470 C₂H₅ CF₃ R3.28 CHF₂ CH₃ I-1471 CH₃ CH₃ R3.29 CHF₂ CH₃ I-1472 C₂H₅ CH₃ R3.29 CHF₂ CH₃ I-1473 CH₃ CHF₂ R3.29 CHF₂ CH₃ I-1474 C₂H₅ CHF₂ R3.29 CHF₂ CH₃ I-1475 CH₃ CF₃ R3.29 CHF₂ CH₃ I-1476 C₂H₅ CF₃ R3.29 CHF₂ CH₃ I-1477 CH₃ CH₃ R3.30 CHF₂ CH₃ I-1478 C₂H₅ CH₃ R3.30 CHF₂ CH₃ I-1479 CH₃ CHF₂ R3.30 CHF₂ CH₃ I-1480 C₂H₅ CHF₂ R3.30 CHF₂ CH₃ I-1481 CH₃ CF₃ R3.30 CHF₂ CH₃ I-1482 C₂H₅ CF₃ R3.30 CHF₂ CH₃ I-1483 CH₃ CH₃ R3.31 CHF₂ CH₃ I-1484 C₂H₅ CH₃ R3.31 CHF₂ CH₃ I-1485 CH₃ CHF₂ R3.31 CHF₂ CH₃ I-1486 C₂H₅ CHF₂ R3.31 CHF₂ CH₃ I-1487 CH₃ CF₃ R3.31 CHF₂ CH₃ I-1488 C₂H₅ CF₃ R3.31 CHF₂ CH₃ I-1489 CH₃ CH₃ R3.32 CHF₂ CH₃ I-1490 C₂H₅ CH₃ R3.32 CHF₂ CH₃ I-1491 CH₃ CHF₂ R3.32 CHF₂ CH₃ I-1492 C₂H₅ CHF₂ R3.32 CHF₂ CH₃ I-1493 CH₃ CF₃ R3.32 CHF₂ CH₃ I-1494 C₂H₅ CF₃ R3.32 CHF₂ CH₃ I-1495 CH₃ CH₃ R3.33 CHF₂ CH₃ I-1496 C₂H₅ CH₃ R3.33 CHF₂ CH₃ I-1497 CH₃ CHF₂ R3.33 CHF₂ CH₃ I-1498 C₂H₅ CHF₂ R3.33 CHF₂ CH₃ I-1499 CH₃ CF₃ R3.33 CHF₂ CH₃ I-1500 C₂H₅ CF₃ R3.33 CHF₂ CH₃ I-1501 CH₃ CH₃ R3.34 CHF₂ CH₃ I-1502 C₂H₅ CH₃ R3.34 CHF₂ CH₃ I-1503 CH₃ CHF₂ R3.34 CHF₂ CH₃ I-1504 C₂H₅ CHF₂ R3.34 CHF₂ CH₃ I-1505 CH₃ CF₃ R3.34 CHF₂ CH₃ I-1506 C₂H₅ CF₃ R3.34 CHF₂ CH₃ I-1507 CH₃ CH₃ R3.35 CHF₂ CH₃ I-1508 C₂H₅ CH₃ R3.35 CHF₂ CH₃ I-1509 CH₃ CHF₂ R3.35 CHF₂ CH₃ I-1510 C₂H₅ CHF₂ R3.35 CHF₂ CH₃ I-1511 CH₃ CF₃ R3.35 CHF₂ CH₃ I-1512 C₂H₅ CF₃ R3.35 CHF₂ CH₃ I-1513 CH₃ CH₃ R3.36 CHF₂ CH₃ I-1514 C₂H₅ CH₃ R3.36 CHF₂ CH₃ I-1515 CH₃ CHF₂ R3.36 CHF₂ CH₃ I-1516 C₂H₅ CHF₂ R3.36 CHF₂ CH₃ I-1517 CH₃ CF₃ R3.36 CHF₂ CH₃ I-1518 C₂H₅ CF₃ R3.36 CHF₂ CH₃ I-1519 CH₃ CH₃ R3.37 CHF₂ CH₃ I-1520 C₂H₅ CH₃ R3.37 CHF₂ CH₃ I-1521 CH₃ CHF₂ R3.37 CHF₂ CH₃ I-1522 C₂H₅ CHF₂ R3.37 CHF₂ CH₃ I-1523 CH₃ CF₃ R3.37 CHF₂ CH₃ I-1524 C₂H₅ CF₃ R3.37 CHF₂ CH₃ I-1525 CH₃ CH₃ R3.38 CHF₂ CH₃ I-1526 C₂H₅ CH₃ R3.38 CHF₂ CH₃ I-1527 CH₃ CHF₂ R3.38 CHF₂ CH₃ I-1528 C₂H₅ CHF₂ R3.38 CHF₂ CH₃ I-1529 CH₃ CF₃ R3.38 CHF₂ CH₃ I-1530 C₂H₅ CF₃ R3.38 CHF₂ CH₃ I-1531 CH₃ CH₃ R3.39 CHF₂ CH₃ I-1532 C₂H₅ CH₃ R3.39 CHF₂ CH₃ I-1533 CH₃ CHF₂ R3.39 CHF₂ CH₃ I-1534 C₂H₅ CHF₂ R3.39 CHF₂ CH₃ I-1535 CH₃ CF₃ R3.39 CHF₂ CH₃ I-1536 C₂H₅ CF₃ R3.39 CHF₂ CH₃ I-1537 CH₃ CH₃ R3.40 CHF₂ CH₃ I-1538 C₂H₅ CH₃ R3.40 CHF₂ CH₃ I-1539 CH₃ CHF₂ R3.40 CHF₂ CH₃ I-1540 C₂H₅ CHF₂ R3.40 CHF₂ CH₃ I-1541 CH₃ CF₃ R3.40 CHF₂ CH₃ I-1542 C₂H₅ CF₃ R3.40 CHF₂ CH₃ I-1543 CH₃ CH₃ R3.41 CHF₂ CH₃ I-1544 C₂H₅ CH₃ R3.41 CHF₂ CH₃ I-1545 CH₃ CHF₂ R3.41 CHF₂ CH₃ I-1546 C₂H₅ CHF₂ R3.41 CHF₂ CH₃ I-1547 CH₃ CF₃ R3.41 CHF₂ CH₃ I-1548 C₂H₅ CF₃ R3.41 CHF₂ CH₃ I-1549 CH₃ CH₃ R3.42 CHF₂ CH₃ I-1550 C₂H₅ CH₃ R3.42 CHF₂ CH₃ I-1551 CH₃ CHF₂ R3.42 CHF₂ CH₃ I-1552 C₂H₅ CHF₂ R3.42 CHF₂ CH₃ I-1553 CH₃ CF₃ R3.42 CHF₂ CH₃ I-1554 C₂H₅ CF₃ R3.42 CHF₂ CH₃ I-1555 CH₃ CH₃ R3.43 CHF₂ CH₃ I-1556 C₂H₅ CH₃ R3.43 CHF₂ CH₃ I-1557 CH₃ CHF₂ R3.43 CHF₂ CH₃ I-1558 C₂H₅ CHF₂ R3.43 CHF₂ CH₃ I-1559 CH₃ CF₃ R3.43 CHF₂ CH₃ I-1560 C₂H₅ CF₃ R3.43 CHF₂ CH₃ I-1561 CH₃ CH₃ 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I-1795 CH₃ CH₃ R3.44 CH₃ CH₃ I-1796 C₂H₅ CH₃ R3.44 CH₃ CH₃ I-1797 CH₃ CHF₂ R3.44 CH₃ CH₃ I-1798 C₂H₅ CHF₂ R3.44 CH₃ CH₃ I-1799 CH₃ CF₃ R3.44 CH₃ CH₃ I-1800 C₂H₅ CF₃ R3.44 CH₃ CH₃ I-1801 CH₃ CH₃ R3.45 CH₃ CH₃ I-1802 C₂H₅ CH₃ R3.45 CH₃ CH₃ I-1803 CH₃ CHF₂ R3.45 CH₃ CH₃ I-1804 C₂H₅ CHF₂ R3.45 CH₃ CH₃ I-1805 CH₃ CF₃ R3.45 CH₃ CH₃ I-1806 C₂H₅ CF₃ R3.45 CH₃ CH₃ I-1807 CH₃ CH₃ R3.46 CH₃ CH₃ I-1808 C₂H₅ CH₃ R3.46 CH₃ CH₃ I-1809 CH₃ CHF₂ R3.46 CH₃ CH₃ I-1810 C₂H₅ CHF₂ R3.46 CH₃ CH₃ I-1811 CH₃ CF₃ R3.46 CH₃ CH₃ I-1812 C₂H₅ CF₃ R3.46 CH₃ CH₃ I-1813 CH₃ CH₃ R3.47 CH₃ CH₃ I-1814 C₂H₅ CH₃ R3.47 CH₃ CH₃ I-1815 CH₃ CHF₂ R3.47 CH₃ CH₃ I-1816 C₂H₅ CHF₂ R3.47 CH₃ CH₃ I-1817 CH₃ CF₃ R3.47 CH₃ CH₃ I-1818 C₂H₅ CF₃ R3.47 CH₃ CH₃ I-1819 CH₃ CH₃ R3.48 CH₃ CH₃ I-1820 C₂H₅ CH₃ R3.48 CH₃ CH₃ I-1821 CH₃ CHF₂ R3.48 CH₃ CH₃ I-1822 C₂H₅ CHF₂ R3.48 CH₃ CH₃ I-1823 CH₃ CF₃ R3.48 CH₃ CH₃ I-1824 C₂H₅ CF₃ R3.48 CH₃ CH₃ I-1825 CH₃ CH₃ R3.10 C₂H₅ CH₃ I-1826 C₂H₅ CH₃ R3.10 C₂H₅ CH₃ I-1827 CH₃ CHF₂ R3.10 C₂H₅ CH₃ I-1828 C₂H₅ CHF₂ R3.10 C₂H₅ CH₃ I-1829 CH₃ CF₃ R3.10 C₂H₅ CH₃ I-1830 C₂H₅ CF₃ R3.10 C₂H₅ CH₃ I-1831 CH₃ CH₃ R3.11 C₂H₅ CH₃ I-1832 C₂H₅ CH₃ R3.11 C₂H₅ CH₃ I-1833 CH₃ CHF₂ R3.11 C₂H₅ CH₃ I-1834 C₂H₅ CHF₂ R3.11 C₂H₅ CH₃ I-1835 CH₃ CF₃ R3.11 C₂H₅ CH₃ I-1836 C₂H₅ CF₃ R3.11 C₂H₅ CH₃ I-1837 CH₃ CH₃ R3.12 C₂H₅ CH₃ I-1838 C₂H₅ CH₃ R3.12 C₂H₅ CH₃ I-1839 CH₃ CHF₂ R3.12 C₂H₅ CH₃ I-1840 C₂H₅ CHF₂ R3.12 C₂H₅ CH₃ I-1841 CH₃ CF₃ R3.12 C₂H₅ CH₃ I-1842 C₂H₅ CF₃ R3.12 C₂H₅ CH₃ I-1843 CH₃ CH₃ R3.13 C₂H₅ CH₃ I-1844 C₂H₅ CH₃ R3.13 C₂H₅ CH₃ I-1845 CH₃ CHF₂ R3.13 C₂H₅ CH₃ I-1846 C₂H₅ CHF₂ R3.13 C₂H₅ CH₃ I-1847 CH₃ CF₃ R3.13 C₂H₅ CH₃ I-1848 C₂H₅ CF₃ R3.13 C₂H₅ CH₃ I-1849 CH₃ CH₃ R3.14 C₂H₅ CH₃ I-1850 C₂H₅ CH₃ R3.14 C₂H₅ CH₃ I-1851 CH₃ CHF₂ R3.14 C₂H₅ CH₃ I-1852 C₂H₅ CHF₂ R3.14 C₂H₅ CH₃ I-1853 CH₃ CF₃ R3.14 C₂H₅ CH₃ I-1854 C₂H₅ CF₃ R3.14 C₂H₅ CH₃ I-1855 CH₃ CH₃ R3.15 C₂H₅ CH₃ I-1856 C₂H₅ CH₃ R3.15 C₂H₅ CH₃ I-1857 CH₃ CHF₂ R3.15 C₂H₅ CH₃ I-1858 C₂H₅ CHF₂ R3.15 C₂H₅ CH₃ I-1859 CH₃ CF₃ R3.15 C₂H₅ CH₃ I-1860 C₂H₅ CF₃ R3.15 C₂H₅ CH₃ I-1861 CH₃ CH₃ R3.16 C₂H₅ CH₃ I-1862 C₂H₅ CH₃ R3.16 C₂H₅ CH₃ I-1863 CH₃ CHF₂ R3.16 C₂H₅ CH₃ I-1864 C₂H₅ CHF₂ R3.16 C₂H₅ CH₃ I-1865 CH₃ CF₃ R3.16 C₂H₅ CH₃ I-1866 C₂H₅ CF₃ R3.16 C₂H₅ CH₃ I-1867 CH₃ CH₃ R3.17 C₂H₅ CH₃ I-1868 C₂H₅ CH₃ R3.17 C₂H₅ CH₃ I-1869 CH₃ CHF₂ R3.17 C₂H₅ CH₃ I-1870 C₂H₅ CHF₂ R3.17 C₂H₅ CH₃ I-1871 CH₃ CF₃ R3.17 C₂H₅ CH₃ I-1872 C₂H₅ CF₃ R3.17 C₂H₅ CH₃ I-1873 CH₃ CH₃ R3.18 C₂H₅ CH₃ I-1874 C₂H₅ CH₃ R3.18 C₂H₅ CH₃ I-1875 CH₃ CHF₂ R3.18 C₂H₅ CH₃ I-1876 C₂H₅ CHF₂ R3.18 C₂H₅ CH₃ I-1877 CH₃ CF₃ R3.18 C₂H₅ CH₃ I-1878 C₂H₅ CF₃ R3.18 C₂H₅ CH₃ I-1879 CH₃ CH₃ R3.19 C₂H₅ CH₃ I-1880 C₂H₅ CH₃ R3.19 C₂H₅ CH₃ I-1881 CH₃ CHF₂ R3.19 C₂H₅ CH₃ I-1882 C₂H₅ CHF₂ R3.19 C₂H₅ CH₃ I-1883 CH₃ CF₃ R3.19 C₂H₅ CH₃ I-1884 C₂H₅ CF₃ R3.19 C₂H₅ CH₃ I-1885 CH₃ CH₃ R3.20 C₂H₅ CH₃ I-1886 C₂H₅ CH₃ R3.20 C₂H₅ CH₃ I-1887 CH₃ CHF₂ R3.20 C₂H₅ CH₃ I-1888 C₂H₅ CHF₂ R3.20 C₂H₅ CH₃ I-1889 CH₃ CF₃ R3.20 C₂H₅ CH₃ I-1890 C₂H₅ CF₃ R3.20 C₂H₅ CH₃ I-1891 CH₃ CH₃ R3.21 C₂H₅ CH₃ I-1892 C₂H₅ CH₃ R3.21 C₂H₅ CH₃ I-1893 CH₃ CHF₂ R3.21 C₂H₅ CH₃ I-1894 C₂H₅ CHF₂ R3.21 C₂H₅ CH₃ I-1895 CH₃ CF₃ R3.21 C₂H₅ CH₃ I-1896 C₂H₅ CF₃ R3.21 C₂H₅ CH₃ I-1897 CH₃ CH₃ R3.22 C₂H₅ CH₃ I-1898 C₂H₅ CH₃ R3.22 C₂H₅ CH₃ I-1899 CH₃ CHF₂ R3.22 C₂H₅ CH₃ I-1900 C₂H₅ CHF₂ R3.22 C₂H₅ CH₃ I-1901 CH₃ CF₃ R3.22 C₂H₅ CH₃ I-1902 C₂H₅ CF₃ R3.22 C₂H₅ CH₃ I-1903 CH₃ CH₃ R3.23 C₂H₅ CH₃ I-1904 C₂H₅ CH₃ R3.23 C₂H₅ CH₃ I-1905 CH₃ CHF₂ R3.23 C₂H₅ CH₃ I-1906 C₂H₅ CHF₂ R3.23 C₂H₅ CH₃ I-1907 CH₃ CF₃ R3.23 C₂H₅ CH₃ I-1908 C₂H₅ CF₃ R3.23 C₂H₅ CH₃ I-1909 CH₃ CH₃ R3.24 C₂H₅ CH₃ I-1910 C₂H₅ CH₃ R3.24 C₂H₅ CH₃ I-1911 CH₃ CHF₂ R3.24 C₂H₅ CH₃ I-1912 C₂H₅ CHF₂ R3.24 C₂H₅ CH₃ I-1913 CH₃ CF₃ R3.24 C₂H₅ CH₃ I-1914 C₂H₅ CF₃ R3.24 C₂H₅ CH₃ I-1915 CH₃ CH₃ R3.25 C₂H₅ CH₃ I-1916 C₂H₅ CH₃ R3.25 C₂H₅ CH₃ I-1917 CH₃ CHF₂ R3.25 C₂H₅ CH₃ I-1918 C₂H₅ CHF₂ R3.25 C₂H₅ CH₃ I-1919 CH₃ CF₃ R3.25 C₂H₅ CH₃ I-1920 C₂H₅ CF₃ R3.25 C₂H₅ CH₃ I-1921 CH₃ CH₃ R3.26 C₂H₅ CH₃ I-1922 C₂H₅ CH₃ R3.26 C₂H₅ CH₃ I-1923 CH₃ CHF₂ R3.26 C₂H₅ CH₃ I-1924 C₂H₅ CHF₂ R3.26 C₂H₅ CH₃ I-1925 CH₃ CF₃ R3.26 C₂H₅ CH₃ I-1926 C₂H₅ CF₃ R3.26 C₂H₅ CH₃ I-1927 CH₃ CH₃ R3.27 C₂H₅ CH₃ I-1928 C₂H₅ CH₃ R3.27 C₂H₅ CH₃ I-1929 CH₃ CHF₂ R3.27 C₂H₅ CH₃ I-1930 C₂H₅ CHF₂ R3.27 C₂H₅ CH₃ I-1931 CH₃ CF₃ R3.27 C₂H₅ CH₃ I-1932 C₂H₅ CF₃ R3.27 C₂H₅ CH₃ I-1933 CH₃ CH₃ R3.28 C₂H₅ CH₃ I-1934 C₂H₅ CH₃ R3.28 C₂H₅ CH₃ I-1935 CH₃ CHF₂ R3.28 C₂H₅ CH₃ I-1936 C₂H₅ CHF₂ R3.28 C₂H₅ CH₃ I-1937 CH₃ CF₃ R3.28 C₂H₅ CH₃ I-1938 C₂H₅ CF₃ R3.28 C₂H₅ CH₃ I-1939 CH₃ CH₃ R3.29 C₂H₅ CH₃ I-1940 C₂H₅ CH₃ R3.29 C₂H₅ CH₃ I-1941 CH₃ CHF₂ R3.29 C₂H₅ CH₃ I-1942 C₂H₅ CHF₂ R3.29 C₂H₅ CH₃ I-1943 CH₃ CF₃ R3.29 C₂H₅ CH₃ I-1944 C₂H₅ CF₃ R3.29 C₂H₅ CH₃ I-1945 CH₃ CH₃ R3.30 C₂H₅ CH₃ I-1946 C₂H₅ CH₃ R3.30 C₂H₅ CH₃ I-1947 CH₃ CHF₂ R3.30 C₂H₅ CH₃ I-1948 C₂H₅ CHF₂ R3.30 C₂H₅ CH₃ I-1949 CH₃ CF₃ R3.30 C₂H₅ CH₃ I-1950 C₂H₅ CF₃ R3.30 C₂H₅ CH₃ I-1951 CH₃ CH₃ R3.31 C₂H₅ CH₃ I-1952 C₂H₅ CH₃ R3.31 C₂H₅ CH₃ I-1953 CH₃ CHF₂ R3.31 C₂H₅ CH₃ I-1954 C₂H₅ CHF₂ R3.31 C₂H₅ CH₃ I-1955 CH₃ CF₃ R3.31 C₂H₅ CH₃ I-1956 C₂H₅ CF₃ R3.31 C₂H₅ CH₃ I-1957 CH₃ CH₃ R3.32 C₂H₅ CH₃ I-1958 C₂H₅ CH₃ R3.32 C₂H₅ CH₃ I-1959 CH₃ CHF₂ R3.32 C₂H₅ CH₃ I-1960 C₂H₅ CHF₂ R3.32 C₂H₅ CH₃ I-1961 CH₃ CF₃ R3.32 C₂H₅ CH₃ I-1962 C₂H₅ CF₃ R3.32 C₂H₅ CH₃ I-1963 CH₃ CH₃ R3.33 C₂H₅ CH₃ I-1964 C₂H₅ CH₃ R3.33 C₂H₅ CH₃ I-1965 CH₃ CHF₂ R3.33 C₂H₅ CH₃ I-1966 C₂H₅ CHF₂ R3.33 C₂H₅ CH₃ I-1967 CH₃ CF₃ R3.33 C₂H₅ CH₃ I-1968 C₂H₅ CF₃ R3.33 C₂H₅ CH₃ I-1969 CH₃ CH₃ R3.34 C₂H₅ CH₃ I-1970 C₂H₅ CH₃ R3.34 C₂H₅ CH₃ I-1971 CH₃ CHF₂ R3.34 C₂H₅ CH₃ I-1972 C₂H₅ CHF₂ R3.34 C₂H₅ CH₃ I-1973 CH₃ CF₃ R3.34 C₂H₅ CH₃ I-1974 C₂H₅ CF₃ R3.34 C₂H₅ CH₃ I-1975 CH₃ CH₃ R3.35 C₂H₅ CH₃ I-1976 C₂H₅ CH₃ R3.35 C₂H₅ CH₃ I-1977 CH₃ CHF₂ R3.35 C₂H₅ CH₃ I-1978 C₂H₅ CHF₂ R3.35 C₂H₅ CH₃ I-1979 CH₃ CF₃ R3.35 C₂H₅ CH₃ I-1980 C₂H₅ CF₃ R3.35 C₂H₅ CH₃ I-1981 CH₃ CH₃ R3.36 C₂H₅ CH₃ I-1982 C₂H₅ CH₃ R3.36 C₂H₅ CH₃ I-1983 CH₃ CHF₂ R3.36 C₂H₅ CH₃ I-1984 C₂H₅ CHF₂ R3.36 C₂H₅ CH₃ I-1985 CH₃ CF₃ R3.36 C₂H₅ CH₃ I-1986 C₂H₅ CF₃ R3.36 C₂H₅ CH₃ I-1987 CH₃ CH₃ R3.37 C₂H₅ CH₃ I-1988 C₂H₅ CH₃ R3.37 C₂H₅ CH₃ I-1989 CH₃ CHF₂ R3.37 C₂H₅ CH₃ I-1990 C₂H₅ CHF₂ R3.37 C₂H₅ CH₃ I-1991 CH₃ CF₃ R3.37 C₂H₅ CH₃ I-1992 C₂H₅ CF₃ R3.37 C₂H₅ CH₃ I-1993 CH₃ CH₃ R3.38 C₂H₅ CH₃ I-1994 C₂H₅ CH₃ R3.38 C₂H₅ CH₃ I-1995 CH₃ CHF₂ R3.38 C₂H₅ CH₃ I-1996 C₂H₅ CHF₂ R3.38 C₂H₅ CH₃ I-1997 CH₃ CF₃ R3.38 C₂H₅ CH₃ I-1998 C₂H₅ CF₃ R3.38 C₂H₅ CH₃ I-1999 CH₃ CH₃ R3.39 C₂H₅ CH₃ I-2000 C₂H₅ CH₃ R3.39 C₂H₅ CH₃ I-2001 CH₃ CHF₂ R3.39 C₂H₅ CH₃ I-2002 C₂H₅ CHF₂ R3.39 C₂H₅ CH₃ I-2003 CH₃ CF₃ R3.39 C₂H₅ CH₃ I-2004 C₂H₅ CF₃ R3.39 C₂H₅ CH₃ I-2005 CH₃ CH₃ R3.40 C₂H₅ CH₃ I-2006 C₂H₅ CH₃ R3.40 C₂H₅ CH₃ I-2007 CH₃ CHF₂ R3.40 C₂H₅ CH₃ I-2008 C₂H₅ CHF₂ R3.40 C₂H₅ CH₃ I-2009 CH₃ CF₃ R3.40 C₂H₅ CH₃ I-2010 C₂H₅ CF₃ R3.40 C₂H₅ CH₃ I-2011 CH₃ CH₃ R3.41 C₂H₅ CH₃ I-2012 C₂H₅ CH₃ R3.41 C₂H₅ CH₃ I-2013 CH₃ CHF₂ R3.41 C₂H₅ CH₃ I-2014 C₂H₅ CHF₂ R3.41 C₂H₅ CH₃ I-2015 CH₃ CF₃ R3.41 C₂H₅ CH₃ I-2016 C₂H₅ CF₃ R3.41 C₂H₅ CH₃ I-2017 CH₃ CH₃ R3.42 C₂H₅ CH₃ I-2018 C₂H₅ CH₃ R3.42 C₂H₅ CH₃ I-2019 CH₃ CHF₂ R3.42 C₂H₅ CH₃ I-2020 C₂H₅ CHF₂ R3.42 C₂H₅ CH₃ I-2021 CH₃ CF₃ R3.42 C₂H₅ CH₃ I-2022 C₂H₅ CF₃ R3.42 C₂H₅ CH₃ I-2023 CH₃ CH₃ R3.43 C₂H₅ CH₃ I-2024 C₂H₅ CH₃ R3.43 C₂H₅ CH₃ I-2025 CH₃ CHF₂ R3.43 C₂H₅ CH₃ I-2026 C₂H₅ CHF₂ R3.43 C₂H₅ CH₃ I-2027 CH₃ CF₃ R3.43 C₂H₅ CH₃ I-2028 C₂H₅ CF₃ R3.43 C₂H₅ CH₃ I-2029 CH₃ CH₃ R3.44 C₂H₅ CH₃ I-2030 C₂H₅ CH₃ R3.44 C₂H₅ CH₃ I-2031 CH₃ CHF₂ R3.44 C₂H₅ CH₃ I-2032 C₂H₅ CHF₂ R3.44 C₂H₅ CH₃ I-2033 CH₃ CF₃ R3.44 C₂H₅ CH₃ I-2034 C₂H₅ CF₃ R3.44 C₂H₅ CH₃ I-2035 CH₃ CH₃ R3.45 C₂H₅ CH₃ I-2036 C₂H₅ CH₃ R3.45 C₂H₅ CH₃ I-2037 CH₃ CHF₂ R3.45 C₂H₅ CH₃ I-2038 C₂H₅ CHF₂ R3.45 C₂H₅ CH₃ I-2039 CH₃ CF₃ R3.45 C₂H₅ CH₃ I-2040 C₂H₅ CF₃ R3.45 C₂H₅ CH₃ I-2041 CH₃ CH₃ R3.46 C₂H₅ CH₃ I-2042 C₂H₅ CH₃ R3.46 C₂H₅ CH₃ I-2043 CH₃ CHF₂ R3.46 C₂H₅ CH₃ I-2044 C₂H₅ CHF₂ R3.46 C₂H₅ CH₃ I-2045 CH₃ CF₃ R3.46 C₂H₅ CH₃ I-2046 C₂H₅ CF₃ R3.46 C₂H₅ CH₃ I-2047 CH₃ CH₃ R3.47 C₂H₅ CH₃ I-2048 C₂H₅ CH₃ R3.47 C₂H₅ CH₃ I-2049 CH₃ CHF₂ R3.47 C₂H₅ CH₃ I-2050 C₂H₅ CHF₂ R3.47 C₂H₅ CH₃ I-2051 CH₃ CF₃ R3.47 C₂H₅ CH₃ I-2052 C₂H₅ CF₃ R3.47 C₂H₅ CH₃ I-2053 CH₃ CH₃ R3.48 C₂H₅ CH₃ I-2054 C₂H₅ CH₃ R3.48 C₂H₅ CH₃ I-2055 CH₃ CHF₂ R3.48 C₂H₅ CH₃ I-2056 C₂H₅ CHF₂ R3.48 C₂H₅ CH₃ I-2057 CH₃ CF₃ R3.48 C₂H₅ CH₃ I-2058 C₂H₅ CF₃ R3.48 C₂H₅ CH₃ I-2059 CH₃ CH₃ R3.10 CF₃ CH₃ I-2060 C₂H₅ CH₃ R3.10 CF₃ CH₃ I-2061 CH₃ CHF₂ R3.10 CF₃ CH₃ I-2062 C₂H₅ CHF₂ R3.10 CF₃ CH₃ I-2063 CH₃ CF₃ R3.10 CF₃ CH₃ I-2064 C₂H₅ CF₃ R3.10 CF₃ CH₃ I-2065 CH₃ CH₃ R3.11 CF₃ CH₃ I-2066 C₂H₅ CH₃ R3.11 CF₃ CH₃ I-2067 CH₃ CHF₂ R3.11 CF₃ CH₃ I-2068 C₂H₅ CHF₂ R3.11 CF₃ CH₃ I-2069 CH₃ CF₃ R3.11 CF₃ CH₃ I-2070 C₂H₅ CF₃ R3.11 CF₃ CH₃ I-2071 CH₃ CH₃ R3.12 CF₃ CH₃ I-2072 C₂H₅ CH₃ R3.12 CF₃ CH₃ I-2073 CH₃ CHF₂ R3.12 CF₃ CH₃ I-2074 C₂H₅ CHF₂ R3.12 CF₃ CH₃ I-2075 CH₃ CF₃ R3.12 CF₃ CH₃ I-2076 C₂H₅ CF₃ R3.12 CF₃ CH₃ I-2077 CH₃ CH₃ R3.13 CF₃ CH₃ I-2078 C₂H₅ CH₃ R3.13 CF₃ CH₃ I-2079 CH₃ CHF₂ R3.13 CF₃ CH₃ I-2080 C₂H₅ CHF₂ R3.13 CF₃ CH₃ I-2081 CH₃ CF₃ R3.13 CF₃ CH₃ I-2082 C₂H₅ CF₃ R3.13 CF₃ CH₃ I-2083 CH₃ CH₃ R3.14 CF₃ CH₃ I-2084 C₂H₅ CH₃ R3.14 CF₃ CH₃ I-2085 CH₃ CHF₂ R3.14 CF₃ CH₃ I-2086 C₂H₅ CHF₂ R3.14 CF₃ CH₃ I-2087 CH₃ CF₃ R3.14 CF₃ CH₃ I-2088 C₂H₅ CF₃ R3.14 CF₃ CH₃ I-2089 CH₃ CH₃ R3.15 CF₃ CH₃ I-2090 C₂H₅ CH₃ R3.15 CF₃ CH₃ I-2091 CH₃ CHF₂ R3.15 CF₃ CH₃ I-2092 C₂H₅ CHF₂ R3.15 CF₃ CH₃ I-2093 CH₃ CF₃ R3.15 CF₃ CH₃ I-2094 C₂H₅ CF₃ R3.15 CF₃ CH₃ I-2095 CH₃ CH₃ R3.16 CF₃ CH₃ I-2096 C₂H₅ CH₃ R3.16 CF₃ CH₃ I-2097 CH₃ CHF₂ R3.16 CF₃ CH₃ I-2098 C₂H₅ CHF₂ R3.16 CF₃ CH₃ I-2099 CH₃ CF₃ R3.16 CF₃ CH₃ I-2100 C₂H₅ CF₃ R3.16 CF₃ CH₃ I-2101 CH₃ CH₃ R3.17 CF₃ CH₃ I-2102 C₂H₅ CH₃ R3.17 CF₃ CH₃ I-2103 CH₃ CHF₂ R3.17 CF₃ CH₃ I-2104 C₂H₅ CHF₂ R3.17 CF₃ CH₃ I-2105 CH₃ CF₃ R3.17 CF₃ CH₃ I-2106 C₂H₅ CF₃ R3.17 CF₃ CH₃ I-2107 CH₃ CH₃ R3.18 CF₃ CH₃ I-2108 C₂H₅ CH₃ R3.18 CF₃ CH₃ I-2109 CH₃ CHF₂ R3.18 CF₃ CH₃ I-2110 C₂H₅ CHF₂ R3.18 CF₃ CH₃ I-2111 CH₃ CF₃ R3.18 CF₃ CH₃ I-2112 C₂H₅ CF₃ R3.18 CF₃ CH₃ I-2113 CH₃ CH₃ R3.19 CF₃ CH₃ I-2114 C₂H₅ CH₃ R3.19 CF₃ CH₃ I-2115 CH₃ CHF₂ R3.19 CF₃ CH₃ I-2116 C₂H₅ CHF₂ R3.19 CF₃ CH₃ I-2117 CH₃ CF₃ R3.19 CF₃ CH₃ I-2118 C₂H₅ CF₃ R3.19 CF₃ CH₃ I-2119 CH₃ CH₃ R3.20 CF₃ CH₃ I-2120 C₂H₅ CH₃ R3.20 CF₃ CH₃ I-2121 CH₃ CHF₂ R3.20 CF₃ CH₃ I-2122 C₂H₅ CHF₂ R3.20 CF₃ CH₃ I-2123 CH₃ CF₃ R3.20 CF₃ CH₃ I-2124 C₂H₅ CF₃ R3.20 CF₃ CH₃ I-2125 CH₃ CH₃ R3.21 CF₃ CH₃ I-2126 C₂H₅ CH₃ R3.21 CF₃ CH₃ I-2127 CH₃ CHF₂ R3.21 CF₃ CH₃ I-2128 C₂H₅ CHF₂ R3.21 CF₃ CH₃ I-2129 CH₃ CF₃ R3.21 CF₃ CH₃ I-2130 C₂H₅ CF₃ R3.21 CF₃ CH₃ I-2131 CH₃ CH₃ R3.22 CF₃ CH₃ I-2132 C₂H₅ CH₃ R3.22 CF₃ CH₃ I-2133 CH₃ CHF₂ R3.22 CF₃ CH₃ I-2134 C₂H₅ CHF₂ R3.22 CF₃ CH₃ I-2135 CH₃ CF₃ R3.22 CF₃ CH₃ I-2136 C₂H₅ CF₃ R3.22 CF₃ CH₃ I-2137 CH₃ CH₃ R3.23 CF₃ CH₃ I-2138 C₂H₅ CH₃ R3.23 CF₃ CH₃ I-2139 CH₃ CHF₂ R3.23 CF₃ CH₃ I-2140 C₂H₅ CHF₂ R3.23 CF₃ CH₃ I-2141 CH₃ CF₃ R3.23 CF₃ CH₃ I-2142 C₂H₅ CF₃ R3.23 CF₃ CH₃ I-2143 CH₃ CH₃ R3.24 CF₃ CH₃ I-2144 C₂H₅ CH₃ R3.24 CF₃ CH₃ I-2145 CH₃ CHF₂ R3.24 CF₃ CH₃ I-2146 C₂H₅ CHF₂ R3.24 CF₃ CH₃ I-2147 CH₃ CF₃ R3.24 CF₃ CH₃ I-2148 C₂H₅ CF₃ R3.24 CF₃ CH₃ I-2149 CH₃ CH₃ R3.25 CF₃ CH₃ I-2150 C₂H₅ CH₃ R3.25 CF₃ CH₃ I-2151 CH₃ CHF₂ R3.25 CF₃ CH₃ I-2152 C₂H₅ CHF₂ R3.25 CF₃ CH₃ I-2153 CH₃ CF₃ R3.25 CF₃ CH₃ I-2154 C₂H₅ CF₃ R3.25 CF₃ CH₃ I-2155 CH₃ CH₃ R3.26 CF₃ CH₃ I-2156 C₂H₅ CH₃ R3.26 CF₃ CH₃ I-2157 CH₃ CHF₂ R3.26 CF₃ CH₃ I-2158 C₂H₅ CHF₂ R3.26 CF₃ CH₃ I-2159 CH₃ CF₃ R3.26 CF₃ CH₃ I-2160 C₂H₅ CF₃ R3.26 CF₃ CH₃ I-2161 CH₃ CH₃ R3.27 CF₃ CH₃ I-2162 C₂H₅ CH₃ R3.27 CF₃ CH₃ I-2163 CH₃ CHF₂ R3.27 CF₃ CH₃ I-2164 C₂H₅ CHF₂ R3.27 CF₃ CH₃ I-2165 CH₃ CF₃ R3.27 CF₃ CH₃ I-2166 C₂H₅ CF₃ R3.27 CF₃ CH₃ I-2167 CH₃ CH₃ R3.28 CF₃ CH₃ I-2168 C₂H₅ CH₃ R3.28 CF₃ CH₃ I-2169 CH₃ CHF₂ R3.28 CF₃ CH₃ I-2170 C₂H₅ CHF₂ R3.28 CF₃ CH₃ I-2171 CH₃ CF₃ R3.28 CF₃ CH₃ I-2172 C₂H₅ CF₃ R3.28 CF₃ CH₃ I-2173 CH₃ CH₃ R3.29 CF₃ CH₃ I-2174 C₂H₅ CH₃ R3.29 CF₃ CH₃ I-2175 CH₃ CHF₂ R3.29 CF₃ CH₃ I-2176 C₂H₅ CHF₂ R3.29 CF₃ CH₃ I-2177 CH₃ CF₃ R3.29 CF₃ CH₃ I-2178 C₂H₅ CF₃ R3.29 CF₃ CH₃ I-2179 CH₃ CH₃ R3.30 CF₃ CH₃ I-2180 C₂H₅ CH₃ R3.30 CF₃ CH₃ I-2181 CH₃ CHF₂ R3.30 CF₃ CH₃ I-2182 C₂H₅ CHF₂ R3.30 CF₃ CH₃ I-2183 CH₃ CF₃ R3.30 CF₃ CH₃ I-2184 C₂H₅ CF₃ R3.30 CF₃ CH₃ I-2185 CH₃ CH₃ R3.31 CF₃ CH₃ I-2186 C₂H₅ CH₃ R3.31 CF₃ CH₃ I-2187 CH₃ CHF₂ R3.31 CF₃ CH₃ I-2188 C₂H₅ CHF₂ R3.31 CF₃ CH₃ I-2189 CH₃ CF₃ R3.31 CF₃ CH₃ I-2190 C₂H₅ CF₃ R3.31 CF₃ CH₃ I-2191 CH₃ CH₃ R3.32 CF₃ CH₃ I-2192 C₂H₅ CH₃ R3.32 CF₃ CH₃ I-2193 CH₃ CHF₂ R3.32 CF₃ CH₃ I-2194 C₂H₅ CHF₂ R3.32 CF₃ CH₃ I-2195 CH₃ CF₃ R3.32 CF₃ CH₃ I-2196 C₂H₅ CF₃ R3.32 CF₃ CH₃ I-2197 CH₃ CH₃ R3.33 CF₃ CH₃ I-2198 C₂H₅ CH₃ R3.33 CF₃ CH₃ I-2199 CH₃ CHF₂ R3.33 CF₃ CH₃ I-2200 C₂H₅ CHF₂ R3.33 CF₃ CH₃ I-2201 CH₃ CF₃ R3.33 CF₃ CH₃ I-2202 C₂H₅ CF₃ R3.33 CF₃ CH₃ I-2203 CH₃ CH₃ R3.34 CF₃ CH₃ I-2204 C₂H₅ CH₃ R3.34 CF₃ CH₃ I-2205 CH₃ CHF₂ R3.34 CF₃ CH₃ I-2206 C₂H₅ CHF₂ R3.34 CF₃ CH₃ I-2207 CH₃ CF₃ R3.34 CF₃ CH₃ I-2208 C₂H₅ CF₃ R3.34 CF₃ CH₃ I-2209 CH₃ CH₃ R3.35 CF₃ CH₃ I-2210 C₂H₅ CH₃ R3.35 CF₃ CH₃ I-2211 CH₃ CHF₂ R3.35 CF₃ CH₃ I-2212 C₂H₅ CHF₂ R3.35 CF₃ CH₃ I-2213 CH₃ CF₃ R3.35 CF₃ CH₃ I-2214 C₂H₅ CF₃ R3.35 CF₃ CH₃ I-2215 CH₃ CH₃ R3.36 CF₃ CH₃ I-2216 C₂H₅ CH₃ R3.36 CF₃ CH₃ I-2217 CH₃ CHF₂ R3.36 CF₃ CH₃ I-2218 C₂H₅ CHF₂ R3.36 CF₃ CH₃ I-2219 CH₃ CF₃ R3.36 CF₃ CH₃ I-2220 C₂H₅ CF₃ R3.36 CF₃ CH₃ I-2221 CH₃ CH₃ R3.37 CF₃ CH₃ I-2222 C₂H₅ CH₃ R3.37 CF₃ CH₃ I-2223 CH₃ CHF₂ R3.37 CF₃ CH₃ I-2224 C₂H₅ CHF₂ R3.37 CF₃ CH₃ I-2225 CH₃ CF₃ R3.37 CF₃ CH₃ I-2226 C₂H₅ CF₃ R3.37 CF₃ CH₃ I-2227 CH₃ CH₃ R3.38 CF₃ CH₃ I-2228 C₂H₅ CH₃ R3.38 CF₃ CH₃ I-2229 CH₃ CHF₂ R3.38 CF₃ CH₃ I-2230 C₂H₅ CHF₂ R3.38 CF₃ CH₃ I-2231 CH₃ CF₃ R3.38 CF₃ CH₃ I-2232 C₂H₅ CF₃ R3.38 CF₃ CH₃ I-2233 CH₃ CH₃ R3.39 CF₃ CH₃ I-2234 C₂H₅ CH₃ R3.39 CF₃ CH₃ I-2235 CH₃ CHF₂ R3.39 CF₃ CH₃ I-2236 C₂H₅ CHF₂ R3.39 CF₃ CH₃ I-2237 CH₃ CF₃ R3.39 CF₃ CH₃ I-2238 C₂H₅ CF₃ R3.39 CF₃ CH₃ I-2239 CH₃ CH₃ R3.40 CF₃ CH₃ I-2240 C₂H₅ CH₃ R3.40 CF₃ CH₃ I-2241 CH₃ CHF₂ R3.40 CF₃ CH₃ I-2242 C₂H₅ CHF₂ R3.40 CF₃ CH₃ I-2243 CH₃ CF₃ R3.40 CF₃ CH₃ I-2244 C₂H₅ CF₃ R3.40 CF₃ CH₃ I-2245 CH₃ CH₃ R3.41 CF₃ CH₃ I-2246 C₂H₅ CH₃ R3.41 CF₃ CH₃ I-2247 CH₃ CHF₂ R3.41 CF₃ CH₃ I-2248 C₂H₅ CHF₂ R3.41 CF₃ CH₃ I-2249 CH₃ CF₃ R3.41 CF₃ CH₃ I-2250 C₂H₅ CF₃ R3.41 CF₃ CH₃ I-2251 CH₃ CH₃ R3.42 CF₃ CH₃ I-2252 C₂H₅ CH₃ R3.42 CF₃ CH₃ I-2253 CH₃ CHF₂ R3.42 CF₃ CH₃ I-2254 C₂H₅ CHF₂ R3.42 CF₃ CH₃ I-2255 CH₃ CF₃ R3.42 CF₃ CH₃ I-2256 C₂H₅ CF₃ R3.42 CF₃ CH₃ I-2257 CH₃ CH₃ R3.43 CF₃ CH₃ I-2258 C₂H₅ CH₃ R3.43 CF₃ CH₃ I-2259 CH₃ CHF₂ R3.43 CF₃ CH₃ I-2260 C₂H₅ CHF₂ R3.43 CF₃ CH₃ I-2261 CH₃ CF₃ R3.43 CF₃ CH₃ I-2262 C₂H₅ CF₃ R3.43 CF₃ CH₃ I-2263 CH₃ CH₃ R3.44 CF₃ CH₃ I-2264 C₂H₅ CH₃ R3.44 CF₃ CH₃ I-2265 CH₃ CHF₂ R3.44 CF₃ CH₃ I-2266 C₂H₅ CHF₂ R3.44 CF₃ CH₃ I-2267 CH₃ CF₃ R3.44 CF₃ CH₃ I-2268 C₂H₅ CF₃ R3.44 CF₃ CH₃ I-2269 CH₃ CH₃ R3.45 CF₃ CH₃ I-2270 C₂H₅ CH₃ R3.45 CF₃ CH₃ I-2271 CH₃ CHF₂ R3.45 CF₃ CH₃ I-2272 C₂H₅ CHF₂ R3.45 CF₃ CH₃ I-2273 CH₃ CF₃ R3.45 CF₃ CH₃ I-2274 C₂H₅ CF₃ R3.45 CF₃ CH₃ I-2275 CH₃ CH₃ R3.46 CF₃ CH₃ I-2276 C₂H₅ CH₃ R3.46 CF₃ CH₃ I-2277 CH₃ CHF₂ R3.46 CF₃ CH₃ I-2278 C₂H₅ CHF₂ R3.46 CF₃ CH₃ I-2279 CH₃ CF₃ R3.46 CF₃ CH₃ I-2280 C₂H₅ CF₃ R3.46 CF₃ CH₃ I-2281 CH₃ CH₃ R3.47 CF₃ CH₃ I-2282 C₂H₅ CH₃ R3.47 CF₃ CH₃ I-2283 CH₃ CHF₂ R3.47 CF₃ CH₃ I-2284 C₂H₅ CHF₂ R3.47 CF₃ CH₃ I-2285 CH₃ CF₃ R3.47 CF₃ CH₃ I-2286 C₂H₅ CF₃ R3.47 CF₃ CH₃ I-2287 CH₃ CH₃ R3.48 CF₃ CH₃ I-2288 C₂H₅ CH₃ R3.48 CF₃ CH₃ I-2289 CH₃ CHF₂ R3.48 CF₃ CH₃ I-2290 C₂H₅ CHF₂ R3.48 CF₃ CH₃ I-2291 CH₃ CF₃ R3.48 CF₃ CH₃ I-2292 C₂H₅ CF₃ R3.48 CF₃ CH₃

TABLE III No. R¹ R² R³ R⁴ R⁵ I-2293 CH₃ CH₃ R3.49 H I-2294 C₂H₅ CH₃ R3.49 H I-2295 CH₃ CHF₂ R3.49 H I-2296 C₂H₅ CHF₂ R3.49 H I-2297 CH₃ CF₃ R3.49 H I-2298 C₂H₅ CF₃ R3.49 H I-2299 CH₃ CH₃ R3.50 H I-2300 C₂H₅ CH₃ R3.50 H I-2301 CH₃ CHF₂ R3.50 H I-2302 C₂H₅ CHF₂ R3.50 H I-2303 CH₃ CF₃ R3.50 H I-2304 C₂H₅ CF₃ R3.50 H I-2305 CH₃ CH₃ R3.51 H I-2306 C₂H₅ CH₃ R3.51 H I-2307 CH₃ CHF₂ R3.51 H I-2308 C₂H₅ CHF₂ R3.51 H I-2309 CH₃ CF₃ R3.51 H I-2310 C₂H₅ CF₃ R3.51 H I-2311 CH₃ CH₃ R3.52 H I-2312 C₂H₅ CH₃ R3.52 H I-2313 CH₃ CHF₂ R3.52 H I-2314 C₂H₅ CHF₂ R3.52 H I-2315 CH₃ CF₃ R3.52 H I-2316 C₂H₅ CF₃ R3.52 H I-2317 CH₃ CH₃ R3.53 H I-2318 C₂H₅ CH₃ R3.53 H I-2319 CH₃ CHF₂ R3.53 H I-2320 C₂H₅ CHF₂ R3.53 H I-2321 CH₃ CF₃ R3.53 H I-2322 C₂H₅ CF₃ R3.53 H I-2323 CH₃ CH₃ R3.49 CH₃ I-2324 C₂H₅ CH₃ R3.49 CH₃ I-2325 CH₃ CHF₂ R3.49 CH₃ I-2326 C₂H₅ CHF₂ R3.49 CH₃ I-2327 CH₃ CF₃ R3.49 CH₃ I-2328 C₂H₅ CF₃ R3.49 CH₃ I-2329 CH₃ CH₃ R3.50 CH₃ I-2330 C₂H₅ CH₃ R3.50 CH₃ I-2331 CH₃ CHF₂ R3.50 CH₃ I-2332 C₂H₅ CHF₂ R3.50 CH₃ I-2333 CH₃ CF₃ R3.50 CH₃ I-2334 C₂H₅ CF₃ R3.50 CH₃ I-2335 CH₃ CH₃ R3.51 CH₃ I-2336 C₂H₅ CH₃ R3.51 CH₃ I-2337 CH₃ CHF₂ R3.51 CH₃ I-2338 C₂H₅ CHF₂ R3.51 CH₃ I-2339 CH₃ CF₃ R3.51 CH₃ I-2340 C₂H₅ CF₃ R3.51 CH₃ I-2341 CH₃ CH₃ R3.52 CH₃ I-2342 C₂H₅ CH₃ R3.52 CH₃ I-2343 CH₃ CHF₂ R3.52 CH₃ I-2344 C₂H₅ CHF₂ R3.52 CH₃ I-2345 CH₃ CF₃ R3.52 CH₃ I-2346 C₂H₅ CF₃ R3.52 CH₃ I-2347 CH₃ CH₃ R3.53 CH₃ I-2348 C₂H₅ CH₃ R3.53 CH₃ I-2349 CH₃ CHF₂ R3.53 CH₃ I-2350 C₂H₅ CHF₂ R3.53 CH₃ I-2351 CH₃ CF₃ R3.53 CH₃ I-2352 C₂H₅ CF₃ R3.53 CH₃ I-2353 CH₃ CH₃ R3.49 CN I-2354 C₂H₅ CH₃ R3.49 CN I-2355 CH₃ CHF₂ R3.49 CN I-2356 C₂H₅ CHF₂ R3.49 CN I-2357 CH₃ CF₃ R3.49 CN I-2358 C₂H₅ CF₃ R3.49 CN I-2359 CH₃ CH₃ R3.50 CN I-2360 C₂H₅ CH₃ R3.50 CN I-2361 CH₃ CHF₂ R3.50 CN I-2362 C₂H₅ CHF₂ R3.50 CN I-2363 CH₃ CF₃ R3.50 CN I-2364 C₂H₅ CF₃ R3.50 CN I-2365 CH₃ CH₃ R3.51 CN I-2366 C₂H₅ CH₃ R3.51 CN I-2367 CH₃ CHF₂ R3.51 CN I-2368 C₂H₅ CHF₂ R3.51 CN I-2369 CH₃ CF₃ R3.51 CN I-2370 C₂H₅ CF₃ R3.51 CN I-2371 CH₃ CH₃ R3.52 CN I-2372 C₂H₅ CH₃ R3.52 CN I-2373 CH₃ CHF₂ R3.52 CN I-2374 C₂H₅ CHF₂ R3.52 CN I-2375 CH₃ CF₃ R3.52 CN I-2376 C₂H₅ CF₃ R3.52 CN I-2377 CH₃ CH₃ R3.53 CN I-2378 C₂H₅ CH₃ R3.53 CN I-2379 CH₃ CHF₂ R3.53 CN I-2380 C₂H₅ CHF₂ R3.53 CN I-2381 CH₃ CF₃ R3.53 CN I-2382 C₂H₅ CF₃ R3.53 CN I-2383 CH₃ CH₃ R3.49 F I-2384 C₂H₅ CH₃ R3.49 F I-2385 CH₃ CHF₂ R3.49 F I-2386 C₂H₅ CHF₂ R3.49 F I-2387 CH₃ CF₃ R3.49 F I-2388 C₂H₅ CF₃ R3.49 F I-2389 CH₃ CH₃ R3.50 F I-2390 C₂H₅ CH₃ R3.50 F I-2391 CH₃ CHF₂ R3.50 F I-2392 C₂H₅ CHF₂ R3.50 F I-2393 CH₃ CF₃ R3.50 F I-2394 C₂H₅ CF₃ R3.50 F I-2395 CH₃ CH₃ R3.51 F I-2396 C₂H₅ CH₃ R3.51 F I-2397 CH₃ CHF₂ R3.51 F I-2398 C₂H₅ CHF₂ R3.51 F I-2399 CH₃ CF₃ R3.51 F I-2400 C₂H₅ CF₃ R3.51 F I-2401 CH₃ CH₃ R3.52 F I-2402 C₂H₅ CH₃ R3.52 F I-2403 CH₃ CHF₂ R3.52 F I-2404 C₂H₅ CHF₂ R3.52 F I-2405 CH₃ CF₃ R3.52 F I-2406 C₂H₅ CF₃ R3.52 F I-2407 CH₃ CH₃ R3.53 F I-2408 C₂H₅ CH₃ R3.53 F I-2409 CH₃ CHF₂ R3.53 F I-2410 C₂H₅ CHF₂ R3.53 F I-2411 CH₃ CF₃ R3.53 F I-2412 C₂H₅ CF₃ R3.53 F I-2413 CH₃ CH₃ R3.49 CF₃ I-2414 C₂H₅ CH₃ R3.49 CF₃ I-2415 CH₃ CHF₂ R3.49 CF₃ I-2416 C₂H₅ CHF₂ R3.49 CF₃ I-2417 CH₃ CF₃ R3.49 CF₃ I-2418 C₂H₅ CF₃ R3.49 CF₃ I-2419 CH₃ CH₃ R3.50 CF₃ I-2420 C₂H₅ CH₃ R3.50 CF₃ I-2421 CH₃ CHF₂ R3.50 CF₃ I-2422 C₂H₅ CHF₂ R3.50 CF₃ I-2423 CH₃ CF₃ R3.50 CF₃ I-2424 C₂H₅ CF₃ R3.50 CF₃ I-2425 CH₃ CH₃ R3.51 CF₃ I-2426 C₂H₅ CH₃ R3.51 CF₃ I-2427 CH₃ CHF₂ R3.51 CF₃ I-2428 C₂H₅ CHF₂ R3.51 CF₃ I-2429 CH₃ CF₃ R3.51 CF₃ I-2430 C₂H₅ CF₃ R3.51 CF₃ I-2431 CH₃ CH₃ R3.52 CF₃ I-2432 C₂H₅ CH₃ R3.52 CF₃ I-2433 CH₃ CHF₂ R3.52 CF₃ I-2434 C₂H₅ CHF₂ R3.52 CF₃ I-2435 CH₃ CF₃ R3.52 CF₃ I-2436 C₂H₅ CF₃ R3.52 CF₃ I-2437 CH₃ CH₃ R3.53 CF₃ I-2438 C₂H₅ CH₃ R3.53 CF₃ I-2439 CH₃ CHF₂ R3.53 CF₃ I-2440 C₂H₅ CHF₂ R3.53 CF₃ I-2441 CH₃ CF₃ R3.53 CF₃ I-2442 C₂H₅ CF₃ R3.53 CF₃ I-2443 CH₃ CH₃ R3.49 OCH₃ I-2444 C₂H₅ CH₃ R3.49 OCH₃ I-2445 CH₃ CHF₂ R3.49 OCH₃ I-2446 C₂H₅ CHF₂ R3.49 OCH₃ I-2447 CH₃ CF₃ R3.49 OCH₃ I-2448 C₂H₅ CF₃ R3.49 OCH₃ I-2449 CH₃ CH₃ R3.50 OCH₃ I-2450 C₂H₅ CH₃ R3.50 OCH₃ I-2451 CH₃ CHF₂ R3.50 OCH₃ I-2452 C₂H₅ CHF₂ R3.50 OCH₃ I-2453 CH₃ CF₃ R3.50 OCH₃ I-2454 C₂H₅ CF₃ R3.50 OCH₃ I-2455 CH₃ CH₃ R3.51 OCH₃ I-2456 C₂H₅ CH₃ R3.51 OCH₃ I-2457 CH₃ CHF₂ R3.51 OCH₃ I-2458 C₂H₅ CHF₂ R3.51 OCH₃ I-2459 CH₃ CF₃ R3.51 OCH₃ I-2460 C₂H₅ CF₃ R3.51 OCH₃ I-2461 CH₃ CH₃ R3.52 OCH₃ I-2462 C₂H₅ CH₃ R3.52 OCH₃ I-2463 CH₃ CHF₂ R3.52 OCH₃ I-2464 C₂H₅ CHF₂ R3.52 OCH₃ I-2465 CH₃ CF₃ R3.52 OCH₃ I-2466 C₂H₅ CF₃ R3.52 OCH₃ I-2467 CH₃ CH₃ R3.53 OCH₃ I-2468 C₂H₅ CH₃ R3.53 OCH₃ I-2469 CH₃ CHF₂ R3.53 OCH₃ I-2470 C₂H₅ CHF₂ R3.53 OCH₃ I-2471 CH₃ CF₃ R3.53 OCH₃ I-2472 C₂H₅ CF₃ R3.53 OCH₃ I-2473 CH₃ CH₃ R3.49 SCH₃ I-2474 C₂H₅ CH₃ R3.49 SCH₃ I-2475 CH₃ CHF₂ R3.49 SCH₃ I-2476 C₂H₅ CHF₂ R3.49 SCH₃ I-2477 CH₃ CF₃ R3.49 SCH₃ I-2478 C₂H₅ CF₃ R3.49 SCH₃ I-2479 CH₃ CH₃ R3.50 SCH₃ I-2480 C₂H₅ CH₃ R3.50 SCH₃ I-2481 CH₃ CHF₂ R3.50 SCH₃ I-2482 C₂H₅ CHF₂ R3.50 SCH₃ I-2483 CH₃ CF₃ R3.50 SCH₃ I-2484 C₂H₅ CF₃ R3.50 SCH₃ I-2485 CH₃ CH₃ R3.51 SCH₃ I-2486 C₂H₅ CH₃ R3.51 SCH₃ I-2487 CH₃ CHF₂ R3.51 SCH₃ I-2488 C₂H₅ CHF₂ R3.51 SCH₃ I-2489 CH₃ CF₃ R3.51 SCH₃ I-2490 C₂H₅ CF₃ R3.51 SCH₃ I-2491 CH₃ CH₃ R3.52 SCH₃ I-2492 C₂H₅ CH₃ R3.52 SCH₃ I-2493 CH₃ CHF₂ R3.52 SCH₃ I-2494 C₂H₅ CHF₂ R3.52 SCH₃ I-2495 CH₃ CF₃ R3.52 SCH₃ I-2496 C₂H₅ CF₃ R3.52 SCH₃ I-2497 CH₃ CH₃ R3.53 SCH₃ I-2498 C₂H₅ CH₃ R3.53 SCH₃ I-2499 CH₃ CHF₂ R3.53 SCH₃ I-2500 C₂H₅ CHF₂ R3.53 SCH₃ I-2501 CH₃ CF₃ R3.53 SCH₃ I-2502 C₂H₅ CF₃ R3.53 SCH₃ I-2503 CH₃ CH₃ R3.49 OCF₃ I-2504 C₂H₅ CH₃ R3.49 OCF₃ I-2505 CH₃ CHF₂ R3.49 OCF₃ I-2506 C₂H₅ CHF₂ R3.49 OCF₃ I-2507 CH₃ CF₃ R3.49 OCF₃ I-2508 C₂H₅ CF₃ R3.49 OCF₃ I-2509 CH₃ CH₃ R3.50 OCF₃ I-2510 C₂H₅ CH₃ R3.50 OCF₃ I-2511 CH₃ CHF₂ R3.50 OCF₃ I-2512 C₂H₅ CHF₂ R3.50 OCF₃ I-2513 CH₃ CF₃ R3.50 OCF₃ I-2514 C₂H₅ CF₃ R3.50 OCF₃ I-2515 CH₃ CH₃ R3.51 OCF₃ I-2516 C₂H₅ CH₃ R3.51 OCF₃ I-2517 CH₃ CHF₂ R3.51 OCF₃ I-2518 C₂H₅ CHF₂ R3.51 OCF₃ I-2519 CH₃ CF₃ R3.51 OCF₃ I-2520 C₂H₅ CF₃ R3.51 OCF₃ I-2521 CH₃ CH₃ R3.52 OCF₃ I-2522 C₂H₅ CH₃ R3.52 OCF₃ I-2523 CH₃ CHF₂ R3.52 OCF₃ I-2524 C₂H₅ CHF₂ R3.52 OCF₃ I-2525 CH₃ CF₃ R3.52 OCF₃ I-2526 C₂H₅ CF₃ R3.52 OCF₃ I-2527 CH₃ CH₃ R3.53 OCF₃ I-2528 C₂H₅ CH₃ R3.53 OCF₃ I-2529 CH₃ CHF₂ R3.53 OCF₃ I-2530 C₂H₅ CHF₂ R3.53 OCF₃ I-2531 CH₃ CF₃ R3.53 OCF₃ I-2532 C₂H₅ CF₃ R3.53 OCF₃ I-2533 CH₃ CH₃ R3.49 SCF₃ I-2534 C₂H₅ CH₃ R3.49 SCF₃ I-2535 CH₃ CHF₂ R3.49 SCF₃ I-2536 C₂H₅ CHF₂ R3.49 SCF₃ I-2537 CH₃ CF₃ R3.49 SCF₃ I-2538 C₂H₅ CF₃ R3.49 SCF₃ I-2539 CH₃ CH₃ R3.50 SCF₃ I-2540 C₂H₅ CH₃ R3.50 SCF₃ I-2541 CH₃ CHF₂ R3.50 SCF₃ I-2542 C₂H₅ CHF₂ R3.50 SCF₃ I-2543 CH₃ CF₃ R3.50 SCF₃ I-2544 C₂H₅ CF₃ R3.50 SCF₃ I-2545 CH₃ CH₃ R3.51 SCF₃ I-2546 C₂H₅ CH₃ R3.51 SCF₃ I-2547 CH₃ CHF₂ R3.51 SCF₃ I-2548 C₂H₅ CHF₂ R3.51 SCF₃ I-2549 CH₃ CF₃ R3.51 SCF₃ I-2550 C₂H₅ CF₃ R3.51 SCF₃ I-2551 CH₃ CH₃ R3.52 SCF₃ I-2552 C₂H₅ CH₃ R3.52 SCF₃ I-2553 CH₃ CHF₂ R3.52 SCF₃ I-2554 C₂H₅ CHF₂ R3.52 SCF₃ I-2555 CH₃ CF₃ R3.52 SCF₃ I-2556 C₂H₅ CF₃ R3.52 SCF₃ I-2557 CH₃ CH₃ R3.53 SCF₃ I-2558 C₂H₅ CH₃ R3.53 SCF₃ I-2559 CH₃ CHF₂ R3.53 SCF₃ I-2560 C₂H₅ CHF₂ R3.53 SCF₃ I-2561 CH₃ CF₃ R3.53 SCF₃ I-2562 C₂H₅ CF₃ R3.53 SCF₃

TABLE IV No R¹ R² R³ R⁴ R⁵ I-2563 CH₃ CH₃ R3.54 H I-2564 C₂H₅ CH₃ R3.54 H I-2565 CH₃ CH₂F R3.54 H I-2566 C₂H₅ CH₂F R3.54 H I-2567 CH₃ CF₃ R3.54 H I-2568 C₂H₅ CF₃ R3.54 H I-2569 CH₃ CH₃ R3.55 H I-2570 C₂H₅ CH₃ R3.55 H I-2571 CH₃ CH₂F R3.55 H I-2572 C₂H₅ CH₂F R3.55 H I-2573 CH₃ CF₃ R3.55 H I-2574 C₂H₅ CF₃ R3.55 H I-2575 CH₃ CH₃ R3.56 H I-2576 C₂H₅ CH₃ R3.56 H I-2577 CH₃ CH₂F R3.56 H I-2578 C₂H₅ CH₂F R3.56 H I-2579 CH₃ CF₃ R3.56 H I-2580 C₂H₅ CF₃ R3.56 H I-2581 CH₃ CH₃ R3.57 H I-2582 C₂H₅ CH₃ R3.57 H I-2583 CH₃ CH₂F R3.57 H I-2584 C₂H₅ CH₂F R3.57 H I-2585 CH₃ CF₃ R3.57 H I-2586 C₂H₅ CF₃ R3.57 H I-2587 CH₃ CH₃ R3.58 H I-2588 C₂H₅ CH₃ R3.58 H I-2589 CH₃ CH₂F R3.58 H I-2590 C₂H₅ CH₂F R3.58 H I-2591 CH₃ CF₃ R3.58 H I-2592 C₂H₅ CF₃ R3.58 H I-2593 CH₃ CH₃ R3.59 H I-2594 C₂H₅ CH₃ R3.59 H I-2595 CH₃ CH₂F R3.59 H I-2596 C₂H₅ CH₂F R3.59 H I-2597 CH₃ CF₃ R3.59 H I-2598 C₂H₅ CF₃ R3.59 H I-2599 CH₃ CH₃ R3.60 H I-2600 C₂H₅ CH₃ R3.60 H I-2601 CH₃ CH₂F R3.60 H I-2602 C₂H₅ CH₂F R3.60 H I-2603 CH₃ CF₃ R3.60 H I-2604 C₂H₅ CF₃ R3.60 H I-2605 CH₃ CH₃ R3.61 H I-2606 C₂H₅ CH₃ R3.61 H I-2607 CH₃ CH₂F R3.61 H I-2608 C₂H₅ CH₂F R3.61 H I-2609 CH₃ CF₃ R3.61 H I-2610 C₂H₅ CF₃ R3.61 H I-2611 CH₃ CH₃ R3.62 H I-2612 C₂H₅ CH₃ R3.62 H I-2613 CH₃ CH₂F R3.62 H I-2614 C₂H₅ CH₂F R3.62 H I-2615 CH₃ CF₃ R3.62 H I-2616 C₂H₅ CF₃ R3.62 H I-2617 CH₃ CH₃ R3.54 CH₃ I-2618 C₂H₅ CH₃ R3.54 CH₃ I-2619 CH₃ CH₂F R3.54 CH₃ I-2620 C₂H₅ CH₂F R3.54 CH₃ I-2621 CH₃ CF₃ R3.54 CH₃ I-2622 C₂H₅ CF₃ R3.54 CH₃ I-2623 CH₃ CH₃ R3.55 CH₃ I-2624 C₂H₅ CH₃ R3.55 CH₃ I-2625 CH₃ CH₂F R3.55 CH₃ I-2626 C₂H₅ CH₂F R3.55 CH₃ I-2627 CH₃ CF₃ R3.55 CH₃ I-2628 C₂H₅ CF₃ R3.55 CH₃ I-2629 CH₃ CH₃ R3.56 CH₃ I-2630 C₂H₅ CH₃ R3.56 CH₃ I-2631 CH₃ CH₂F R3.56 CH₃ I-2632 C₂H₅ CH₂F R3.56 CH₃ I-2633 CH₃ CF₃ R3.56 CH₃ I-2634 C₂H₅ CF₃ R3.56 CH₃ I-2635 CH₃ CH₃ R3.57 CH₃ I-2636 C₂H₅ CH₃ R3.57 CH₃ I-2637 CH₃ CH₂F R3.57 CH₃ I-2638 C₂H₅ CH₂F R3.57 CH₃ I-2639 CH₃ CF₃ R3.57 CH₃ I-2640 C₂H₅ CF₃ R3.57 CH₃ I-2641 CH₃ CH₃ R3.58 CH₃ I-2642 C₂H₅ CH₃ R3.58 CH₃ I-2643 CH₃ CH₂F R3.58 CH₃ I-2644 C₂H₅ CH₂F R3.58 CH₃ I-2645 CH₃ CF₃ R3.58 CH₃ I-2646 C₂H₅ CF₃ R3.58 CH₃ I-2647 CH₃ CH₃ R3.59 CH₃ I-2648 C₂H₅ CH₃ R3.59 CH₃ I-2649 CH₃ CH₂F R3.59 CH₃ I-2650 C₂H₅ CH₂F R3.59 CH₃ I-2651 CH₃ CF₃ R3.59 CH₃ I-2652 C₂H₅ CF₃ R3.59 CH₃ I-2653 CH₃ CH₃ R3.60 CH₃ I-2654 C₂H₅ CH₃ R3.60 CH₃ I-2655 CH₃ CH₂F R3.60 CH₃ I-2656 C₂H₅ CH₂F R3.60 CH₃ I-2657 CH₃ CF₃ R3.60 CH₃ I-2658 C₂H₅ CF₃ R3.60 CH₃ I-2659 CH₃ CH₃ R3.61 CH₃ I-2660 C₂H₅ CH₃ R3.61 CH₃ I-2661 CH₃ CH₂F R3.61 CH₃ I-2662 C₂H₅ CH₂F R3.61 CH₃ I-2663 CH₃ CF₃ R3.61 CH₃ I-2664 C₂H₅ CF₃ R3.61 CH₃ I-2665 CH₃ CH₃ R3.62 CH₃ I-2666 C₂H₅ CH₃ R3.62 CH₃ I-2667 CH₃ CH₂F R3.62 CH₃ I-2668 C₂H₅ CH₂F R3.62 CH₃ I-2669 CH₃ CF₃ R3.62 CH₃ I-2670 C₂H₅ CF₃ R3.62 CH₃ I-2671 CH₃ CH₃ R3.54 CN I-2672 C₂H₅ CH₃ R3.54 CN I-2673 CH₃ CH₂F R3.54 CN I-2674 C₂H₅ CH₂F R3.54 CN I-2675 CH₃ CF₃ R3.54 CN I-2676 C₂H₅ CF₃ R3.54 CN I-2677 CH₃ CH₃ R3.55 CN I-2678 C₂H₅ CH₃ R3.55 CN I-2679 CH₃ CH₂F R3.55 CN I-2680 C₂H₅ CH₂F R3.55 CN I-2681 CH₃ CF₃ R3.55 CN I-2682 C₂H₅ CF₃ R3.55 CN I-2683 CH₃ CH₃ R3.56 CN I-2684 C₂H₅ CH₃ R3.56 CN I-2685 CH₃ CH₂F R3.56 CN I-2686 C₂H₅ CH₂F R3.56 CN I-2687 CH₃ CF₃ R3.56 CN I-2688 C₂H₅ CF₃ R3.56 CN I-2689 CH₃ CH₃ R3.57 CN I-2690 C₂H₅ CH₃ R3.57 CN I-2691 CH₃ CH₂F R3.57 CN I-2692 C₂H₅ CH₂F R3.57 CN I-2693 CH₃ CF₃ R3.57 CN I-2694 C₂H₅ CF₃ R3.57 CN I-2695 CH₃ CH₃ R3.58 CN I-2696 C₂H₅ CH₃ R3.58 CN I-2697 CH₃ CH₂F R3.58 CN I-2698 C₂H₅ CH₂F R3.58 CN I-2699 CH₃ CF₃ R3.58 CN I-2700 C₂H₅ CF₃ R3.58 CN I-2701 CH₃ CH₃ R3.59 CN I-2702 C₂H₅ CH₃ R3.59 CN I-2703 CH₃ CH₂F R3.59 CN I-2704 C₂H₅ CH₂F R3.59 CN I-2705 CH₃ CF₃ R3.59 CN I-2706 C₂H₅ CF₃ R3.59 CN I-2707 CH₃ CH₃ R3.60 CN I-2708 C₂H₅ CH₃ R3.60 CN I-2709 CH₃ CH₂F R3.60 CN I-2710 C₂H₅ CH₂F R3.60 CN I-2711 CH₃ CF₃ R3.60 CN I-2712 C₂H₅ CF₃ R3.60 CN I-2713 CH₃ CH₃ R3.61 CN I-2714 C₂H₅ CH₃ R3.61 CN I-2715 CH₃ CH₂F R3.61 CN I-2716 C₂H₅ CH₂F R3.61 CN I-2717 CH₃ CF₃ R3.61 CN I-2718 C₂H₅ CF₃ R3.61 CN I-2719 CH₃ CH₃ R3.62 CN I-2720 C₂H₅ CH₃ R3.62 CN I-2721 CH₃ CH₂F R3.62 CN I-2722 C₂H₅ CH₂F R3.62 CN I-2723 CH₃ CF₃ R3.62 CN I-2724 C₂H₅ CF₃ R3.62 CN

The examples of compounds of formula I of table I include their tautomers, racemic mixtures, individual pure enantiomers and diasteroemers and their optically active mixtures.

Some of the compounds of the formula I are novel. Thus the present invention also relates to the novel compounds I-S as defined above.

In compounds I-S, R¹ is preferably H, C₁-C₂-alkyl, or C₁-C₂-alkoxymethyl, in particular CH₃ or C₂H₅. R² is preferably CH₃, CHF₂, or CF₃.

In compounds I-S, the variable R³ is preferably a monospiro or dispiro 5-, 6-, 7-, 8-, 9- or 10-membered carbocycle which is unsubstituted or substituted by 1 or 2 radicals R^(a3). R^(a3), if present, is preferably selected from cyano, C₁-C₂-haloalkyl, C₁-C₂-alkylidene and C₁-C₂-alkoxy-C₁-C₂-alkyl. Substituents R^(a3) are preferably in 1- or 4-position, if the carbocycle is monosubstituted and in 4,4-position, if the carbocycle is disubstituted. More preferably, R³ is spiro[2.2]pentyl, which is unsubstituted or carries one or two radicals R^(a3) or 7-dispiro[2.0.1.2]-heptyl which is unsubstituted or carries a radical R^(a3). R³ is even more preferably selected from the group consisting of spiro[2.2]pentyl (R3.1), 2-methylene-spiro[2.2]pentyl (R3.2), 1-CN-spiro[2.2]pentyl (R3.3), 1-(CF₃)-spiro[2.2]pentyl (R3.4), 4,4-(CH₃)₂-spiro[2.2]pentyl (R3.5), 4-CH₃-spiro[2.2]pentyl (R3.6), 4-(CF₃)-spiro[2.2]pentyl (R3.7), 4-(CH₂OCH₃)-spiro[2.2]pentyl (R3.8), and 7-dispiro[2.0.2.1]-heptyl (R3.9).

In compounds I-S, the variable R⁴ is preferably C₁-C₄-alkyl or C₁-C4-haloalkyl, in particular CH₃, C₂H₅, CHF₂, or CF₃.

In compounds 1-S, the variable R⁵ is preferably H, CH₃, CN, F, OCH₃, SCH₃, CF₃, OCF₃, or SCF₃

Examples for compounds I-S are compounds I-1 to I-432 compiled in table I above.

Specific compounds of this embodiment are compiled in table V below.

TABLE V No. R¹ R² R³ R⁴ R⁵ V-1 H CH₃ spiro[2.2]pentyl CH₃ H V-2 CH₃ CH₃ spiro[2.2]pentyl CH₃ H V-3 CH₂CH₃ CH₃ spiro[2.2]pentyl CH₃ H V-4 H CH₃ 1-CN-spiro[2.2]pentyl CH₃ H V-5 CH₃ CH₃ 1-CN-spiro[2.2]pentyl CH₃ H V-6 CH₂CH₃ CH₃ 1-CN-spiro[2.2]pentyl CH₃ H V-7 H CH₃ 4,4-(CH₃)₂-spiro[2.2]pentyl CH₃ H V-8 CH₃ CH₃ 4,4-(CH₃)₂-spiro[2.2]pentyl CH₃ H V-9 CH₂CH₃ CH₃ 4,4-(CH₃)₂-spiro[2.2]pentyl CH₃ H V-10 H CH₃ 4-(CH₂OCH₃)-spiro[2.2]pentyl CH₃ H V-11 CH₃ CH₃ 4-(CH₂OCH₃)-spiro[2.2]pentyl CH₃ H V-12 CH₂CH₃ CH₃ 4-(CH₂OCH₃)-spiro[2.2]pentyl CH₃ H V-13 H CH₃ 1-[C(═O)NH₂]-spiro[2.2]pentyl CH₃ H V-14 CH₃ CH₃ 1-[C(═O)NH₂]-spiro[2.2]pentyl CH₃ H V-15 CH₂CH₃ CH₃ 1-[C(═O)NH₂]-spiro[2.2]pentyl CH₃ H

The present invention also relates to compounds I-S as defined above:

In compounds I-S′, the variable R¹ is preferably H, C₁-C₂-alkyl, or C₁-C₂-alkoxymethyl, in particular CH₃ or C₂H₅. In compounds I-S′, the variable R² is preferably CH₃, CHF₂, or CF₃. In compounds I-S′, the variable R⁵ is preferably H, CH₃, CN, F, OCH₃, SCH₃, CF₃, OCF₃, or SCF₃.

In compounds I-S′, the variables R³ and R⁴ together with the carbon atom, to which they are attached, form a monospiro or dispiro 5-, 6-, 7-, 8-, 9- or 10-membered carbo- or heterocycle, which may contain 1 or 2 heteroatom moieties selected from N—R^(c), O, and S(O)_(k), with k being 0, 1 or 2, which monospiro or dispiro 5- to 10-membered carbo- or heterocycle is unsubstituted or may be substituted by 1, 2, 3 or 4 radicals R^(a3). R^(a3), if present, is preferably selected from CN, C₁-C₂-haloalkyl, C₁-C₂-alkylidene, and C₁-C₂-alkoxy-C₁-C₂-alkyl. In another embodiment R^(a3) is haloalkyl, preferably CHF₂, or CF₃, preferred CF₃. Substituents R^(a3) are preferably in 1- or 4-position, if the carbocycle is monosubstituted and in 4,4-position, if the carbocycle is disubstituted. More preferably, R³ and R⁴ together with the carbon atom, to which they are attached, form a monospiro or dispiro 5-, 6-, 7-, 8-, 9- or 10-membered carbocycle which is unsubstituted or substituted by 1 or 2 radicals R^(a3). Even more preferably, R³ and R⁴ together with the carbon atom, to which they are attached, form spiro[2.2]pentyl, which is unsubstituted or carries 1 or 2 radicals R^(a3) or 7-dispiro[2.0.1.2]-heptyl which is unsubstituted or carries a radical R^(a3). Specially, R³ and R⁴ together with the carbon atom, to which they are attached, form a radical selected from spiro[2.2]pentyl (R3.54), 2-methylene-spiro[2.2]pentyl (R3.55), 1-CN-spiro[2.2]pentyl (R3.56), 1-CF₃-spiro[2.2]pentyl (R3.57), 4,4-(CH₃)₂-spiro[2.2]pentyl (R3.58), 4-CH₃-spiro[2.2]pentyl (R3.59), 4-(CF₃)-spiro[2.2]pentyl (R3.60) 4-(CH₂OCH₃)-spiro[2.2]pentyl (R3.61), and 7-dispiro[2.0.1.2]-heptyl (R3.62).

Examples of compounds I-S are compounds I-2563 to I-2724 compiled in table IV above. Specific examples are compiled in table VI below:

TABLE VI No. R¹ R² R³ R⁴ R⁵ VI-1 H CH₃ spiro[2.2]pentyl H VI-2 CH₃ CH₃ spiro[2.2]pentyl H VI-3 CH₂CH₃ CH₃ spiro[2.2]pentyl H VI-4 H CH₃ 7-dispiro[2.0.1.2]-heptyl H VI-5 CH₃ CH₃ 7-dispiro[2.0.1.2]-heptyl H VI-6 CH₂CH₃ CH₃ 7-dispiro[2.0.1.2]-heptyl H VI-7 H CH₃ 4,4-(CH₃)₂-spiro[2.2]pentyl H VI-8 CH₃ CH₃ 4,4-(CH₃)₂-spiro[2.2]pentyl H VI-9 CH₂CH₃ CH₃ 4,4-(CH₃)₂-spiro[2.2]pentyl H VI-10 H CH₃ 4-CH₃-spiro[2.2]pentyl H VI-11 CH₃ CH₃ 4-CH₃-spiro[2.2]pentyl H VI-12 CH₂CH₃ CH₃ 4-CH₃-spiro[2.2]pentyl H VI-13 H CH₃ 4-(CF₃)-spiro[2.2]pentyl H VI-14 CH₃ CH₃ 4-(CF₃)-spiro[2.2]pentyl H VI-15 CH₂CH₃ CH₃ 4-(CF₃)-spiro[2.2]pentyl H VI-16 H CH₃ 4-(CH₂OCH₃)-spiro[2.2]pentyl H VI-17 CH₃ CH₃ 4-(CH₂OCH₃)-spiro[2.2]pentyl H VI-18 CH₂CH₃ CH₃ 4-(CH₂OCH₃)-spiro[2.2]pentyl H VI-19 H CH₃ 2-methylene-spiro[2.2]pentyl H VI-20 CH₃ CH₃ 2-methylene-spiro[2.2]pentyl H VI-21 CH₂CH₃ CH₃ 2-methylene-spiro[2.2]pentyl H VI-22 H CH₃ 1,4-dioxaspiro[4.5]decan-8-yl H VI-23 CH₃ CH₃ 1,4-dioxaspiro[4.5]decan-8-yl H VI-24 CH₂CH₃ CH₃ 1,4-dioxaspiro[4.5]decan-8-yl H VI-25 H CH₃ 5-oxaspiro[2.5]octan-8-yl H VI-26 CH₃ CH₃ 5-oxaspiro[2.5]octan-8-yl H VI-27 CH₂CH₃ CH₃ 5-oxaspiro[2.5]octan-8-yl H VI-28 H CH₃ 5,8-dioxaspiro[3.4]octan-2-yl H VI-29 CH₃ CH₃ 5,8-dioxaspiro[3.4]octan-2-yl H VI-30 CH₂CH₃ CH₃ 5,8-dioxaspiro[3.4]octan-2-yl H

The present invention also relates to compounds of the formula I, which are selected from the compounds of the following groups I-a, I-b, I-c and I-d as defined above.

The present invention also relates to compounds of the formula I, which are selected from the compounds of the following groups I-a, I-c and I-d.

In an embodiment, the invention relates to compounds of the group I-a.

In another embodiment, the invention relates to compounds of the group I-b.

In another embodiment, the invention relates to compounds of the group I-c.

In another embodiment, the invention relates to compounds of the group I-d.

In compounds I-a, the variable R³ is a variable R3.10, R3.11, R3.12, R3.13, R3.14, R3.15 or R3.16 as defined above. Examples of the compounds I-a are the compounds I-433 to I-474 and I-1363 to I-1398 compiled in table II.

In compounds I-b, the variable R³ is a variable R3.17, R3.18, R3.19, R3.20, R3.21, R3.22, R3.23, R3.24, R3.25, R3.26, R3.27, R3.28, R3.29, R3.30, R3.31, R3.32, R3.33, R3.34, R3.35, R3.36, R3.37, R3.38, R3.39, R3.40, R3.41, R3.42, R3.43, R3.44, or R3.45 as defined above. In compounds I-b, the variable R³ is preferably a variable R3.18, R3.20, R3.21, R3.24, R3.25, R3.26, R3.27, R3.28, R3.30, R3.31, R3.33, R3.34, R3.35, R3.36, R3.37, R3.38, R3.39, R3.41, R3.42, or R3.43 as defined above. Examples of compounds I-b are the compounds I-475 to I-648, I-705 to I-714, I-717 to I-732, I-735 to I-738, I-741 to I-742, I-744 to I-792, I-793 to I-822, I-825 to I-864, I-867 to I-876, I-931 to I-1104, I-1165 to I-1338, I-1399 to I-1572, I-1633 to I-1806, I-1867 to I-2040, and I-2101 to I-2274 compiled in table II. A preferred group of examples of compounds I-b are the compounds I-475 to I-648, I-705, I-706, I-709 to I-714, I-717, I-718, I-721 to I-732, I-735, I-736, I-741 to I-742, I-745 to I-774, I-777, I-778, I-781 to I-792, I-795, I-796, I-799 to I-822, I-825 to I-840, I-843, I-844, I-847 to I-864, I-867, I-868, I-873, I-874, I-931 to I-1104, I-1167, I-1168, I-1171 to I-1176, I-1179, I-1180, I-1183 to I-1194, I-1197, I-1198, I-1203, I-1204, I-1207 to I-1236, I-1239, I-1240, I-1243 to I-1254, I-1257, I-1258, I-1261 to I-1302, I-1305, I-1306, I-1309 to I-1326, I-1329, I-1330, I-1335, I-1336, I-1399 to I-1572, I-1633 to I-1806, I-1867 to I-2040, and I-2101 to I-2274 compiled in table II.

In compounds I-c, the variables R³ and R⁴ together are a variable R3.49, R3.50 or R3.51 as defined above. Examples of compounds I-c are compiled in table III as compounds I-2293 to I-2310, I-2323 to I-2340, I-2353 to I-2370, I-2383 to I-2400, I-2413 to I-2430, I-2443 to I-2460, I-2473 to I-2490, I-2503 to I-2521 and I-2534 to I-2550.

In compounds I-d, the variables R³ and R⁴ together are a variable R3.52 and R3.53 as defined above. Examples of compounds I-d are compiled in table III as compounds I-2311 to I-2322, I-2341 to I-2352, I-2371 to I-2382, I-2401 to I-2412, I-2431 to I-2442, I-2461 to I-2472, I-2491 to I-2502, I-2521 to I-2532 and I-2551 to I-2562.

The compounds according to the invention can be prepared analogously to the synthesis routes described in WO 2009/027393 and WO 2010/034737 according to standard processes of organic chemistry, for example according to the following synthesis route:

Compounds of formula I, can be prepared e.g. by reacting activated pyrazole carboxylic acid derivative II with a 3-aminopyridine, or 4-aminopyridazine of formula III (e.g. Houben-Weyl: “Methoden der organ. Chemie” [Methods of Organic Chemistry], Georg-Thieme-Verlag, Stuttgart, N.Y. 1985, Volume E5, pp. 941-1045) as out-lined in scheme 1

In scheme 1, R¹, R², R³, R⁴ and R⁵ are as defined above. Activated pyrazole carboxylic acid derivatives II are preferably halides, activated esters, anhydrides, azides, for example chlorides, fluorides, bromides, para-nitrophenyl esters, pentafluorophenyl esters, N-hydroxysuccinimides, hydroxybenzotriazol-1-ylesters. For example, X is a suitable leaving group such as halogen, N₃, p-nitrophenoxy or pentafluorophenoxy and the like.

Compounds of formula I, wherein R¹ is different from hydrogen can also be prepared by alkylating the amides I, in which R¹ is hydrogen, using suitable alkylating agents in the presence of bases. The alkylation can be effected under standard conditions known from literature.

Formula I compounds may be present in three isomeric forms:

For reasons of clarity it is referred to isomer T-A only throughout the specification, but its description embraces disclosure of the other isomers as well.

Isomer T-C can be obtained by alkylation of compounds I, wherein R¹ is hydrogen. The reaction can be performed by analogy to known N-alkylation of pyridazines. N-alkylation of pyridazines is known in literature and can be found in e.g.: J. Chem. Soc., Perkin Trans. Vol. 1, p. 401 (1988), and J. Org. Chem. Vol. 46, p. 2467 (1981). The compounds II and III are known in the art or are commercially available or can be prepared by methods known from the literature (cf. WO 05/040169; WO 08/074824; Journal of Fluorine chemistry 132(11), p. 995 (2011)).

N-oxides of the compounds of formula I, can be prepared by oxidation of compounds I according to standard methods of preparing heteroaromatic N-oxides, e.g. by the method described in Journal of Organometallic Chemistry 1989, 370, 17-31.

If individual compounds cannot be prepared via the above-described routes, they can be prepared by derivatization of other compounds I or by customary modifications of the synthesis routes described. For example, in individual cases, certain compounds I can advantageously be prepared from other compounds I by ester hydrolysis, amidation, esterification, ether cleavage, olefination, reduction, oxidation and the like.

The reaction mixtures are worked up in the customary manner, for example by mixing with water, separating the phases, and, if appropriate, purifying the crude products by chromatography, for example on alumina or on silica gel. Some of the intermediates and end products may be obtained in the form of colorless or pale brown viscous oils which are freed or purified from volatile components under reduced pressure and at moderately elevated temperature. If the intermediates and end products are obtained as solids, they may be purified by recrystallization or trituration.

A particular group of preferred embodiments of the invention are pesticidal combinations, where the pyrazole compound A is a compound of formula I, a stereoisomer, salt, tautomer or N-oxides thereof, wherein the variables R¹, R², R³, R⁴ and R⁵ have the following meanings: R¹ is CH₃, or C₂H₅; R² is CH₃; R³ is CH(CH₃)₂, CHF₂, 1-cyanocyclopropyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-cyano-1-methylethyl, 1-fluoroethyl or spiro[2.2]pentyl, 1-cyanospiro[2.2]pentyl; R⁴ is CH₃, or R³ and R⁴ together with the carbon atom, to which they are bound, form a spiro[2.2]pentyl radical; and R⁵ is H or CN.

Especially preferred embodiments of the invention are pesticidal combinations wherein in each case the pyrazole compound A is selected from a compound of the formula I, where R¹ is C₂H₅, R² is CH₃, R³ is CHF₂, R⁴ is CH₃ and R⁵ is H (compound I-680); a compound of the formula I, where R¹ is C₂H₅, R² is CH₃, R³ is 1-CN-c-C₃H₄, R⁴ is CH₃ and R⁵ is H (compound I-698); a compound of the formula I, where R¹ is CH₃, R² is CH₃, R³ is CH(CH₃)₂, R⁴ is CH₃ and R⁵ is H (compound I-673); and a compound of the formula I, where R¹ is C₂H₅, R² is CH₃, R³ is CH(CH₃)₂, R⁴ is CH₃ and R⁵ is H (compound I-674).

Further especially preferred embodiments of the invention are pesticidal combinations wherein in each case the pyrazole compound A selected from compounds I is selected from compounds I-1, I-2, I-13, I-14, I-679, I-697, I-775, I-776, I-793, I-794, I-871, I-872, I-877, 878, I-2563, I-2564, I-2671 and I-2672.

One embodiment of the invention relates to pesticidal mixtures of at least a compound of formula I with at least one compound B from the groups A.1 to A.17.

A preferred embodiment of the invention relates to pesticidal mixtures of a compound of formula I with one compound B from the groups A.1 to A.17.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.1.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.2.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.3.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.4.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.5.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.6.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.7.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.8.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.9.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.10.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.11.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.12.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.13.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.14.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.15.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.16.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group A.17.

Binary mixtures of a compound of formula I and a compound B from the groups A.1 to A.17 are one preferred embodiment of the invention.

Ternary mixtures of a compound of formula I and two compounds B from the groups A.1 to A.17 are another preferred embodiment of the invention.

With respect to their use in the pesticidal mixtures of the present invention, particular preference is given to the compounds B from the groups A.1 to A.17 as listed in the paragraphs below:

The compound B selected from group A.2 as defined above is preferably acrinathrin, bifenthrin, cyfluthrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, flucythrinate, tau-fluvalinate, silafluofen or tralomethrin.

The compound B selected from group A.3 as defined above is preferably acetamiprid, clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram or thiacloprid.

The compound B selected from group A.4 as defined above is preferably ethiprole or fipronil.

The compound B selected from group A.5 as defined above is preferably abamectin, emamectin benzoate or lepimectin.

The compound B selected from group A.6 as defined above is preferably chlorfenapyr.

The compound B selected from group A.8 as defined above is preferably flonicamid or pymetrozine.

The compound B selected from group A.10 as defined above is preferably spiromesifen or spirotetramat,

The compound B selected from group A.11 as defined above is preferably flubendiamide.

The compound B selected from group A.13 as defined above is preferably chloranthraniliprole (rynaxypyr) or cyantraniliprole.

The compound B selected from group A.16 as defined above is preferably 4-{[(6-chloropyrid-3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-on (A16.3).

The compound B selected from group A.17 is preferably pyrifluquinazon, sulfoxaflor or afidopyropen (cyclopropaneacetic acid, [(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-[[(2-cyclopropylacetyl)oxy]methyl]-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-12-hydroxy-4,6a,12b-trimethyl-11-oxo-9-(3-pyridinyl)-2H,11H-naphtho[2,1-b]pyrano[3,4-e]pyran-3,6-diyl]ester).

A particular group of embodiments of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group consisting of fipronil, alpha-cypermethrin, thiamethoxam, abamectin, spirotetramat, imidacloprid, flonicamid, chloranthraniliprole, pymetrozine, sulfoxaflor and afidopyropen.

In another embodiment, the invention relates to mixtures of a compound of formula I with at least one active compound B selected from the group consisting of the compound A17.3, and A17.4a) to A17.4h): A17.3) 3,4-dihydro-2,4-dioxo-1-(pyrimidin-5-yl-methyl)-3-[3-(trifluoromethyl)phenyl]-2Hpyrido[1,2-a]pyrimidin-1-ium-3-ide, A17.4a)N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; A17.4b)N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoro-methyl)pyrazole-3-carboxamide; A17.4c)N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; A17.4d)N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; A17.4e)N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(difluoromethyl)pyrazole-3-carboxamide; A17.4f)N-[4,6-dibromo-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; A17.4g)N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-cyano-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; A17.4h)N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide.

Especially preferred are inventive mixtures wherein the compound B is fipronil and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is alpha-cypermethrin and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is thiamethoxam and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is abamectin and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is spirotetramat and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is imidacloprid and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is flonicamid and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is chloranthraniliprole (rynaxypyr) and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is pymetrozine and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is sulfoxaflor and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is afidopyren and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

The following table M-I represents preferred combinations of the active compounds I of formula I as defined in Tables I, II, III, or IV and the active compounds B in mixtures according to the invention

TABLE M-I No. Comp. I Comp. B M.1 I-1 acrinathrin M.2 I-2 acrinathrin M.3 I-13 acrinathrin M.4 I-14 acrinathrin M.5 I-673 acrinathrin M.6 I-674 acrinathrin M.7 I-679 acrinathrin M.8 I-680 acrinathrin M.9 I-697 acrinathrin M.10 I-698 acrinathrin M.11 I-775 acrinathrin M.12 I-776 acrinathrin M.13 I-793 acrinathrin M.14 I-794 acrinathrin M.15 I-871 acrinathrin M.16 I-872 acrinathrin M.17 I-877 acrinathrin M.18 I-878 acrinathrin M.19 I-2563 acrinathrin M.20 I-2564 acrinathrin M.21 I-2671 acrinathrin M.22 I-2672 acrinathrin M.23 I-1 bifenthrin M.24 I-2 bifenthrin M.25 I-13 bifenthrin M.26 I-14 bifenthrin M.27 I-673 bifenthrin M.28 I-674 bifenthrin M.29 I-679 bifenthrin M.30 I-680 bifenthrin M.31 I-697 bifenthrin M.32 I-698 bifenthrin M.33 I-775 bifenthrin M.34 I-776 bifenthrin M.35 I-793 bifenthrin M.36 I-794 bifenthrin M.37 I-871 bifenthrin M.38 I-872 bifenthrin M.39 I-877 bifenthrin M.40 I-878 bifenthrin M.41 I-2563 bifenthrin M.42 I-2564 bifenthrin M.43 I-2671 bifenthrin M.44 I-2672 bifenthrin M.45 I-1 cyfluthrin M.46 I-2 cyfluthrin M.47 I-13 cyfluthrin M.48 I-14 cyfluthrin M.49 I-673 cyfluthrin M.50 I-674 cyfluthrin M.51 I-679 cyfluthrin M.52 I-680 cyfluthrin M.53 I-697 cyfluthrin M.54 I-698 cyfluthrin M.55 I-775 cyfluthrin M.56 I-776 cyfluthrin M.57 I-793 cyfluthrin M.58 I-794 cyfluthrin M.59 I-871 cyfluthrin M.60 I-872 cyfluthrin M.61 I-877 cyfluthrin M.62 I-878 cyfluthrin M.63 I-2563 cyfluthrin M.64 I-2564 cyfluthrin M.65 I-2671 cyfluthrin M.66 I-2672 cyfluthrin M.67 I-1 lambda-cyhalothrin M.68 I-2 lambda-cyhalothrin M.69 I-13 lambda-cyhalothrin M.70 I-14 lambda-cyhalothrin M.71 I-673 lambda-cyhalothrin M.72 I-674 lambda-cyhalothrin M.73 I-679 lambda-cyhalothrin M.74 I-680 lambda-cyhalothrin M.75 I-697 lambda-cyhalothrin M.76 I-698 lambda-cyhalothrin M.77 I-775 lambda-cyhalothrin M.78 I-776 lambda-cyhalothrin M.79 I-793 lambda-cyhalothrin M.80 I-794 lambda-cyhalothrin M.81 I-871 lambda-cyhalothrin M.82 I-872 lambda-cyhalothrin M.83 I-877 lambda-cyhalothrin M.84 I-878 lambda-cyhalothrin M.85 I-2563 lambda-cyhalothrin M.86 I-2564 lambda-cyhalothrin M.87 I-2671 lambda-cyhalothrin M.88 I-2672 lambda-cyhalothrin M.89 I-1 cypermethrin M.90 I-2 cypermethrin M.91 I-13 cypermethrin M.92 I-14 cypermethrin M.93 I-673 cypermethrin M.94 I-674 cypermethrin M.95 I-679 cypermethrin M.96 I-680 cypermethrin M.97 I-697 cypermethrin M.98 I-698 cypermethrin M.99 I-775 cypermethrin M.100 I-776 cypermethrin M.101 I-793 cypermethrin M.102 I-794 cypermethrin M.103 I-871 cypermethrin M.104 I-872 cypermethrin M.105 I-877 cypermethrin M.106 I-878 cypermethrin M.107 I-2563 cypermethrin M.108 I-2564 cypermethrin M.109 I-2671 cypermethrin M.110 I-2672 cypermethrin M.111 I-1 alpha-cypermethrin M.112 I-2 alpha-cypermethrin M.113 I-13 alpha-cypermethrin M.114 I-14 alpha-cypermethrin M.115 I-673 alpha-cypermethrin M.116 I-674 alpha-cypermethrin M.117 I-679 alpha-cypermethrin M.118 I-680 alpha-cypermethrin M.119 I-697 alpha-cypermethrin M.120 I-698 alpha-cypermethrin M.121 I-775 alpha-cypermethrin M.122 I-776 alpha-cypermethrin M.123 I-793 alpha-cypermethrin M.124 I-794 alpha-cypermethrin M.125 I-871 alpha-cypermethrin M.126 I-872 alpha-cypermethrin M.127 I-877 alpha-cypermethrin M.128 I-878 alpha-cypermethrin M.129 I-2563 alpha-cypermethrin M.130 I-2564 alpha-cypermethrin M.131 I-2671 alpha-cypermethrin M.132 I-2672 alpha-cypermethrin M.133 I-1 beta-cypermethrin M.134 I-2 beta-cypermethrin M.135 I-13 beta-cypermethrin M.136 I-14 beta-cypermethrin M.137 I-673 beta-cypermethrin M.138 I-674 beta-cypermethrin M.139 I-679 beta-cypermethrin M.140 I-680 beta-cypermethrin M.141 I-697 beta-cypermethrin M.142 I-698 beta-cypermethrin M.143 I-775 beta-cypermethrin M.144 I-776 beta-cypermethrin M.145 I-793 beta-cypermethrin M.146 I-794 beta-cypermethrin M.147 I-871 beta-cypermethrin M.148 I-872 beta-cypermethrin M.149 I-877 beta-cypermethrin M.150 I-878 beta-cypermethrin M.151 I-2563 beta-cypermethrin M.152 I-2564 beta-cypermethrin M.153 I-2671 beta-cypermethrin M.154 I-2672 beta-cypermethrin M.155 I-1 zeta-cypermethrin M.156 I-2 zeta-cypermethrin M.157 I-13 zeta-cypermethrin M.158 I-14 zeta-cypermethrin M.159 I-673 zeta-cypermethrin M.160 I-674 zeta-cypermethrin M.161 I-679 zeta-cypermethrin M.162 I-680 zeta-cypermethrin M.163 I-697 zeta-cypermethrin M.164 I-698 zeta-cypermethrin M.165 I-775 zeta-cypermethrin M.166 I-776 zeta-cypermethrin M.167 I-793 zeta-cypermethrin M.168 I-794 zeta-cypermethrin M.169 I-871 zeta-cypermethrin M.170 I-872 zeta-cypermethrin M.171 I-877 zeta-cypermethrin M.172 I-878 zeta-cypermethrin M.173 I-2563 zeta-cypermethrin M.174 I-2564 zeta-cypermethrin M.175 I-2671 zeta-cypermethrin M.176 I-2672 zeta-cypermethrin M.177 I-1 deltamethrin M.178 I-2 deltamethrin M.179 I-13 deltamethrin M.180 I-14 deltamethrin M.181 I-673 deltamethrin M.182 I-674 deltamethrin M.183 I-679 deltamethrin M.184 I-680 deltamethrin M.185 I-697 deltamethrin M.186 I-698 deltamethrin M.187 I-775 deltamethrin M.188 I-776 deltamethrin M.189 I-793 deltamethrin M.190 I-794 deltamethrin M.191 I-871 deltamethrin M.192 I-872 deltamethrin M.193 I-877 deltamethrin M.194 I-878 deltamethrin M.195 I-2563 deltamethrin M.196 I-2564 deltamethrin M.197 I-2671 deltamethrin M.198 I-2672 deltamethrin M.199 I-1 esfenvalerate M.200 I-2 esfenvalerate M.201 I-13 esfenvalerate M.202 I-14 esfenvalerate M.203 I-673 esfenvalerate M.204 I-674 esfenvalerate M.205 I-679 esfenvalerate M.206 I-680 esfenvalerate M.207 I-697 esfenvalerate M.208 I-698 esfenvalerate M.209 I-775 esfenvalerate M.210 I-776 esfenvalerate M.211 I-793 esfenvalerate M.212 I-794 esfenvalerate M.213 I-871 esfenvalerate M.214 I-872 esfenvalerate M.215 I-877 esfenvalerate M.216 I-878 esfenvalerate M.217 I-2563 esfenvalerate M.218 I-2564 esfenvalerate M.219 I-2671 esfenvalerate M.220 I-2672 esfenvalerate M.221 I-1 etofenprox M.222 I-2 etofenprox M.223 I-13 etofenprox M.224 I-14 etofenprox M.225 I-673 etofenprox M.226 I-674 etofenprox M.227 I-679 etofenprox M.228 I-680 etofenprox M.229 I-697 etofenprox M.230 I-698 etofenprox M.231 I-775 etofenprox M.232 I-776 etofenprox M.233 I-793 etofenprox M.234 I-794 etofenprox M.235 I-871 etofenprox M.236 I-872 etofenprox M.237 I-877 etofenprox M.238 I-878 etofenprox M.239 I-2563 etofenprox M.240 I-2564 etofenprox M.241 I-2671 etofenprox M.242 I-2672 etofenprox M.243 I-1 fenpropathrin M.244 I-2 fenpropathrin M.245 I-13 fenpropathrin M.246 I-14 fenpropathrin M.247 I-673 fenpropathrin M.248 I-674 fenpropathrin M.249 I-679 fenpropathrin M.250 I-680 fenpropathrin M.251 I-697 fenpropathrin M.252 I-698 fenpropathrin M.253 I-775 fenpropathrin M.254 I-776 fenpropathrin M.255 I-793 fenpropathrin M.256 I-794 fenpropathrin M.257 I-871 fenpropathrin M.258 I-872 fenpropathrin M.259 I-877 fenpropathrin M.260 I-878 fenpropathrin M.261 I-2563 fenpropathrin M.262 I-2564 fenpropathrin M.263 I-2671 fenpropathrin M.264 I-2672 fenpropathrin M.265 I-1 flucythrinate M.266 I-2 flucythrinate M.267 I-13 flucythrinate M.268 I-14 flucythrinate M.269 I-673 flucythrinate M.270 I-674 flucythrinate M.271 I-679 flucythrinate M.272 I-680 flucythrinate M.273 I-697 flucythrinate M.274 I-698 flucythrinate M.275 I-775 flucythrinate M.276 I-776 flucythrinate M.277 I-793 flucythrinate M.278 I-794 flucythrinate M.279 I-871 flucythrinate M.280 I-872 flucythrinate M.281 I-877 flucythrinate M.282 I-878 flucythrinate M.283 I-2563 flucythrinate M.284 I-2564 flucythrinate M.285 I-2671 flucythrinate M.286 I-2672 flucythrinate M.287 I-1 tau-fluvalinate M.288 I-2 tau-fluvalinate M.289 I-13 tau-fluvalinate M.290 I-14 tau-fluvalinate M.291 I-673 tau-fluvalinate M.292 I-674 tau-fluvalinate M.293 I-679 tau-fluvalinate M.294 I-680 tau-fluvalinate M.295 I-697 tau-fluvalinate M.296 I-698 tau-fluvalinate M.297 I-775 tau-fluvalinate M.298 I-776 tau-fluvalinate M.299 I-793 tau-fluvalinate M.300 I-794 tau-fluvalinate M.301 I-871 tau-fluvalinate M.302 I-872 tau-fluvalinate M.303 I-877 tau-fluvalinate M.304 I-878 tau-fluvalinate M.305 I-2563 tau-fluvalinate M.306 I-2564 tau-fluvalinate M.307 I-2671 tau-fluvalinate M.308 I-2672 tau-fluvalinate M.309 I-1 silafluofen M.310 I-2 silafluofen M.311 I-13 silafluofen M.312 I-14 silafluofen M.313 I-673 silafluofen M.314 I-674 silafluofen M.315 I-679 silafluofen M.316 I-680 silafluofen M.317 I-697 silafluofen M.318 I-698 silafluofen M.319 I-775 silafluofen M.320 I-776 silafluofen M.321 I-793 silafluofen M.322 I-794 silafluofen M.323 I-871 silafluofen M.324 I-872 silafluofen M.325 I-877 silafluofen M.326 I-878 silafluofen M.327 I-2563 silafluofen M.328 I-2564 silafluofen M.329 I-2671 silafluofen M.330 I-2672 silafluofen M.331 I-1 tralomethrin M.332 I-2 tralomethrin M.333 I-13 tralomethrin M.334 I-14 tralomethrin M.335 I-673 tralomethrin M.336 I-674 tralomethrin M.337 I-679 tralomethrin M.338 I-680 tralomethrin M.339 I-697 tralomethrin M.340 I-698 tralomethrin M.341 I-775 tralomethrin M.342 I-776 tralomethrin M.343 I-793 tralomethrin M.344 I-794 tralomethrin M.345 I-871 tralomethrin M.346 I-872 tralomethrin M.347 I-877 tralomethrin M.348 I-878 tralomethrin M.349 I-2563 tralomethrin M.350 I-2564 tralomethrin M.351 I-2671 tralomethrin M.352 I-2672 tralomethrin M.353 I-1 acetamiprid M.354 I-2 acetamiprid M.355 I-13 acetamiprid M.356 I-14 acetamiprid M.357 I-673 acetamiprid M.358 I-674 acetamiprid M.359 I-679 acetamiprid M.360 I-680 acetamiprid M.361 I-697 acetamiprid M.362 I-698 acetamiprid M.363 I-775 acetamiprid M.364 I-776 acetamiprid M.365 I-793 acetamiprid M.366 I-794 acetamiprid M.367 I-871 acetamiprid M.368 I-872 acetamiprid M.369 I-877 acetamiprid M.370 I-878 acetamiprid M.371 I-2563 acetamiprid M.372 I-2564 acetamiprid M.373 I-2671 acetamiprid M.374 I-2672 acetamiprid M.375 I-1 clothianidin M.376 I-2 clothianidin M.377 I-13 clothianidin M.378 I-14 clothianidin M.379 I-673 clothianidin M.380 I-674 clothianidin M.381 I-679 clothianidin M.382 I-680 clothianidin M.383 I-697 clothianidin M.384 I-698 clothianidin M.385 I-775 clothianidin M.386 I-776 clothianidin M.387 I-793 clothianidin M.388 I-794 clothianidin M.389 I-871 clothianidin M.390 I-872 clothianidin M.391 I-877 clothianidin M.392 I-878 clothianidin M.393 I-2563 clothianidin M.394 I-2564 clothianidin M.395 I-2671 clothianidin M.396 I-2672 clothianidin M.397 I-1 dinotefuran M.398 I-2 dinotefuran M.399 I-13 dinotefuran M.400 I-14 dinotefuran M.401 I-673 dinotefuran M.402 I-674 dinotefuran M.403 I-679 dinotefuran M.404 I-680 dinotefuran M.405 I-697 dinotefuran M.406 I-698 dinotefuran M.407 I-775 dinotefuran M.408 I-776 dinotefuran M.409 I-793 dinotefuran M.410 I-794 dinotefuran M.411 I-871 dinotefuran M.412 I-872 dinotefuran M.413 I-877 dinotefuran M.414 I-878 dinotefuran M.415 I-2563 dinotefuran M.416 I-2564 dinotefuran M.417 I-2671 dinotefuran M.418 I-2672 dinotefuran M.419 I-1 imidacloprid M.420 I-2 imidacloprid M.421 I-13 imidacloprid M.422 I-14 imidacloprid M.423 I-673 imidacloprid M.424 I-674 imidacloprid M.425 I-679 imidacloprid M.426 I-680 imidacloprid M.427 I-697 imidacloprid M.428 I-698 imidacloprid M.429 I-775 imidacloprid M.430 I-776 imidacloprid M.431 I-793 imidacloprid M.432 I-794 imidacloprid M.433 I-871 imidacloprid M.434 I-872 imidacloprid M.435 I-877 imidacloprid M.436 I-878 imidacloprid M.437 I-2563 imidacloprid M.438 I-2564 imidacloprid M.439 I-2671 imidacloprid M.440 I-2672 imidacloprid M.441 I-1 thiamethoxam M.442 I-2 thiamethoxam M.443 I-13 thiamethoxam M.444 I-14 thiamethoxam M.445 I-673 thiamethoxam M.446 I-674 thiamethoxam M.447 I-679 thiamethoxam M.448 I-680 thiamethoxam M.449 I-697 thiamethoxam M.450 I-698 thiamethoxam M.451 I-775 thiamethoxam M.452 I-776 thiamethoxam M.453 I-793 thiamethoxam M.454 I-794 thiamethoxam M.455 I-871 thiamethoxam M.456 I-872 thiamethoxam M.457 I-877 thiamethoxam M.458 I-878 thiamethoxam M.459 I-2563 thiamethoxam M.460 I-2564 thiamethoxam M.461 I-2671 thiamethoxam M.462 I-2672 thiamethoxam M.463 I-1 nitenpyram M.464 I-2 nitenpyram M.465 I-13 nitenpyram M.466 I-14 nitenpyram M.467 I-673 nitenpyram M.468 I-674 nitenpyram M.469 I-679 nitenpyram M.470 I-680 nitenpyram M.471 I-697 nitenpyram M.472 I-698 nitenpyram M.473 I-775 nitenpyram M.474 I-776 nitenpyram M.475 I-793 nitenpyram M.476 I-794 nitenpyram M.477 I-871 nitenpyram M.478 I-872 nitenpyram M.479 I-877 nitenpyram M.480 I-878 nitenpyram M.481 I-2563 nitenpyram M.482 I-2564 nitenpyram M.483 I-2671 nitenpyram M.484 I-2672 nitenpyram M.485 I-1 thiacloprid M.486 I-2 thiacloprid M.487 I-13 thiacloprid M.488 I-14 thiacloprid M.489 I-673 thiacloprid M.490 I-674 thiacloprid M.491 I-679 thiacloprid M.492 I-680 thiacloprid M.493 I-697 thiacloprid M.494 I-698 thiacloprid M.495 I-775 thiacloprid M.496 I-776 thiacloprid M.497 I-793 thiacloprid M.498 I-794 thiacloprid M.499 I-871 thiacloprid M.500 I-872 thiacloprid M.501 I-877 thiacloprid M.502 I-878 thiacloprid M.503 I-2563 thiacloprid M.504 I-2564 thiacloprid M.505 I-2671 thiacloprid M.506 I-2672 thiacloprid M.507 I-1 ethiprole M.508 I-2 ethiprole M.509 I-13 ethiprole M.510 I-14 ethiprole M.511 I-673 ethiprole M.512 I-674 ethiprole M.513 I-679 ethiprole M.514 I-680 ethiprole M.515 I-697 ethiprole M.516 I-698 ethiprole M.517 I-775 ethiprole M.518 I-776 ethiprole M.519 I-793 ethiprole M.520 I-794 ethiprole M.521 I-871 ethiprole M.522 I-872 ethiprole M.523 I-877 ethiprole M.524 I-878 ethiprole M.525 I-2563 ethiprole M.526 I-2564 ethiprole M.527 I-2671 ethiprole M.528 I-2672 ethiprole M.529 I-1 fipronil M.530 I-2 fipronil M.531 I-13 fipronil M.532 I-14 fipronil M.533 I-673 fipronil M.534 I-674 fipronil M.535 I-679 fipronil M.536 I-680 fipronil M.537 I-697 fipronil M.538 I-698 fipronil M.539 I-775 fipronil M.540 I-776 fipronil M.541 I-793 fipronil M.542 I-794 fipronil M.543 I-871 fipronil M.544 I-872 fipronil M.545 I-877 fipronil M.546 I-878 fipronil M.547 I-2563 fipronil M.548 I-2564 fipronil M.549 I-2671 fipronil M.550 I-2672 fipronil M.551 I-1 abamectin M.552 I-2 abamectin M.553 I-13 abamectin M.554 I-14 abamectin M.555 I-673 abamectin M.556 I-674 abamectin M.557 I-679 abamectin M.558 I-680 abamectin M.559 I-697 abamectin M.560 I-698 abamectin M.561 I-775 abamectin M.562 I-776 abamectin M.563 I-793 abamectin M.564 I-794 abamectin M.565 I-871 abamectin M.566 I-872 abamectin M.567 I-877 abamectin M.568 I-878 abamectin M.569 I-2563 abamectin M.570 I-2564 abamectin M.571 I-2671 abamectin M.572 I-2672 abamectin M.573 I-1 emamectin benzoate M.574 I-2 emamectin benzoate M.575 I-13 emamectin benzoate M.576 I-14 emamectin benzoate M.577 I-673 emamectin benzoate M.578 I-674 emamectin benzoate M.579 I-679 emamectin benzoate M.580 I-680 emamectin benzoate M.581 I-697 emamectin benzoate M.582 I-698 emamectin benzoate M.583 I-775 emamectin benzoate M.584 I-776 emamectin benzoate M.585 I-793 emamectin benzoate M.586 I-794 emamectin benzoate M.587 I-871 emamectin benzoate M.588 I-872 emamectin benzoate M.589 I-877 emamectin benzoate M.590 I-878 emamectin benzoate M.591 I-2563 emamectin benzoate M.592 I-2564 emamectin benzoate M.593 I-2671 emamectin benzoate M.594 I-2672 emamectin benzoate M.595 I-1 lepimectin M.596 I-2 lepimectin M.597 I-13 lepimectin M.598 I-14 lepimectin M.599 I-673 lepimectin M.600 I-674 lepimectin M.601 I-679 lepimectin M.602 I-680 lepimectin M.603 I-697 lepimectin M.604 I-698 lepimectin M.605 I-775 lepimectin M.606 I-776 lepimectin M.607 I-793 lepimectin M.608 I-794 lepimectin M.609 I-871 lepimectin M.610 I-872 lepimectin M.611 I-877 lepimectin M.612 I-878 lepimectin M.613 I-2563 lepimectin M.614 I-2564 lepimectin M.615 I-2671 lepimectin M.616 I-2672 lepimectin M.617 I-1 chlorfenapyr M.618 I-2 chlorfenapyr M.619 I-13 chlorfenapyr M.620 I-14 chlorfenapyr M.621 I-673 chlorfenapyr M.622 I-674 chlorfenapyr M.623 I-679 chlorfenapyr M.624 I-680 chlorfenapyr M.625 I-697 chlorfenapyr M.626 I-698 chlorfenapyr M.627 I-775 chlorfenapyr M.628 I-776 chlorfenapyr M.629 I-793 chlorfenapyr M.630 I-794 chlorfenapyr M.631 I-871 chlorfenapyr M.632 I-872 chlorfenapyr M.633 I-877 chlorfenapyr M.634 I-878 chlorfenapyr M.635 I-2563 chlorfenapyr M.636 I-2564 chlorfenapyr M.637 I-2671 chlorfenapyr M.638 I-2672 chlorfenapyr M.639 I-1 flonicamid M.640 I-2 flonicamid M.641 I-13 flonicamid M.642 I-14 flonicamid M.643 I-673 flonicamid M.644 I-674 flonicamid M.645 I-679 flonicamid M.646 I-680 flonicamid M.647 I-697 flonicamid M.648 I-698 flonicamid M.649 I-775 flonicamid M.650 I-776 flonicamid M.651 I-793 flonicamid M.652 I-794 flonicamid M.653 I-871 flonicamid M.654 I-872 flonicamid M.655 I-877 flonicamid M.656 I-878 flonicamid M.657 I-2563 flonicamid M.658 I-2564 flonicamid M.659 I-2671 flonicamid M.660 I-2672 flonicamid M.661 I-1 pymetrozine M.662 I-2 pymetrozine M.663 I-13 pymetrozine M.664 I-14 pymetrozine M.665 I-673 pymetrozine M.666 I-674 pymetrozine M.667 I-679 pymetrozine M.668 I-680 pymetrozine M.669 I-697 pymetrozine M.670 I-698 pymetrozine M.671 I-775 pymetrozine M.672 I-776 pymetrozine M.673 I-793 pymetrozine M.674 I-794 pymetrozine M.675 I-871 pymetrozine M.676 I-872 pymetrozine M.677 I-877 pymetrozine M.678 I-878 pymetrozine M.679 I-2563 pymetrozine M.680 I-2564 pymetrozine M.681 I-2671 pymetrozine M.682 I-2672 pymetrozine M.683 I-1 spiromesifen M.684 I-2 spiromesifen M.685 I-13 spiromesifen M.686 I-14 spiromesifen M.687 I-673 spiromesifen M.688 I-674 spiromesifen M.689 I-679 spiromesifen M.690 I-680 spiromesifen M.691 I-697 spiromesifen M.692 I-698 spiromesifen M.693 I-775 spiromesifen M.694 I-776 spiromesifen M.695 I-793 spiromesifen M.696 I-794 spiromesifen M.697 I-871 spiromesifen M.698 I-872 spiromesifen M.699 I-877 spiromesifen M.700 I-878 spiromesifen M.701 I-2563 spiromesifen M.702 I-2564 spiromesifen M.703 I-2671 spiromesifen M.704 I-2672 spiromesifen M.705 I-1 spirotetramat M.706 I-2 spirotetramat M.707 I-13 spirotetramat M.708 I-14 spirotetramat M.709 I-673 spirotetramat M.710 I-674 spirotetramat M.711 I-679 spirotetramat M.712 I-680 spirotetramat M.713 I-697 spirotetramat M.714 I-698 spirotetramat M.715 I-775 spirotetramat M.716 I-776 spirotetramat M.717 I-793 spirotetramat M.718 I-794 spirotetramat M.719 I-871 spirotetramat M.720 I-872 spirotetramat M.721 I-877 spirotetramat M.722 I-878 spirotetramat M.723 I-2563 spirotetramat M.724 I-2564 spirotetramat M.725 I-2671 spirotetramat M.726 I-2672 spirotetramat M.727 I-1 flubendiamide M.728 I-2 flubendiamide M.729 I-13 flubendiamide M.730 I-14 flubendiamide M.731 I-673 flubendiamide M.732 I-674 flubendiamide M.733 I-679 flubendiamide M.734 I-680 flubendiamide M.735 I-697 flubendiamide M.736 I-698 flubendiamide M.737 I-775 flubendiamide M.738 I-776 flubendiamide M.739 I-793 flubendiamide M.740 I-794 flubendiamide M.741 I-871 flubendiamide M.742 I-872 flubendiamide M.743 I-877 flubendiamide M.744 I-878 flubendiamide M.745 I-2563 flubendiamide M.746 I-2564 flubendiamide M.747 I-2671 flubendiamide M.748 I-2672 flubendiamide M.749 I-1 chloranthraniliprole M.750 I-2 chloranthraniliprole M.751 I-13 chloranthraniliprole M.752 I-14 chloranthraniliprole M.753 I-673 chloranthraniliprole M.754 I-674 chloranthraniliprole M.755 I-679 chloranthraniliprole M.756 I-680 chloranthraniliprole M.757 I-697 chloranthraniliprole M.758 I-698 chloranthraniliprole M.759 I-775 chloranthraniliprole M.760 I-776 chloranthraniliprole M.761 I-793 chloranthraniliprole M.762 I-794 chloranthraniliprole M.763 I-871 chloranthraniliprole M.764 I-872 chloranthraniliprole M.765 I-877 chloranthraniliprole M.766 I-878 chloranthraniliprole M.767 I-2563 chloranthraniliprole M.768 I-2564 chloranthraniliprole M.769 I-2671 chloranthraniliprole M.770 I-2672 chloranthraniliprole M.771 I-1 cyantraniliprole M.772 I-2 cyantraniliprole M.773 I-13 cyantraniliprole M.774 I-14 cyantraniliprole M.775 I-673 cyantraniliprole M.776 I-674 cyantraniliprole M.777 I-679 cyantraniliprole M.778 I-680 cyantraniliprole M.779 I-697 cyantraniliprole M.780 I-698 cyantraniliprole M.781 I-775 cyantraniliprole M.782 I-776 cyantraniliprole M.783 I-793 cyantraniliprole M.784 I-794 cyantraniliprole M.785 I-871 cyantraniliprole M.786 I-872 cyantraniliprole M.787 I-877 cyantraniliprole M.788 I-878 cyantraniliprole M.789 I-2563 cyantraniliprole M.790 I-2564 cyantraniliprole M.791 I-2671 cyantraniliprole M.792 I-2672 cyantraniliprole M.793 I-1 A16.3 M.794 I-2 A16.3 M.795 I-13 A16.3 M.796 I-14 A16.3 M.797 I-673 A16.3 M.798 I-674 A16.3 M.799 I-679 A16.3 M.800 I-680 A16.3 M.801 I-697 A16.3 M.802 I-698 A16.3 M.803 I-775 A16.3 M.804 I-776 A16.3 M.805 I-793 A16.3 M.806 I-794 A16.3 M.807 I-871 A16.3 M.808 I-872 A16.3 M.809 I-877 A16.3 M.810 I-878 A16.3 M.811 I-2563 A16.3 M.812 I-2564 A16.3 M.813 I-2671 A16.3 M.814 I-2672 A16.3 M.815 I-1 pyrifluquinazon M.816 I-2 pyrifluquinazon M.817 I-13 pyrifluquinazon M.818 I-14 pyrifluquinazon M.819 I-673 pyrifluquinazon M.820 I-674 pyrifluquinazon M.821 I-679 pyrifluquinazon M.822 I-680 pyrifluquinazon M.823 I-697 pyrifluquinazon M.824 I-698 pyrifluquinazon M.825 I-775 pyrifluquinazon M.826 I-776 pyrifluquinazon M.827 I-793 pyrifluquinazon M.828 I-794 pyrifluquinazon M.829 I-871 pyrifluquinazon M.830 I-872 pyrifluquinazon M.831 I-877 pyrifluquinazon M.832 I-878 pyrifluquinazon M.833 I-2563 pyrifluquinazon M.834 I-2564 pyrifluquinazon M.835 I-2671 pyrifluquinazon M.836 I-2672 pyrifluquinazon M.837 I-1 sulfoxaflor M.838 I-2 sulfoxaflor M.839 I-13 sulfoxaflor M.840 I-14 sulfoxaflor M.841 I-673 sulfoxaflor M.842 I-674 sulfoxaflor M.843 I-679 sulfoxaflor M.844 I-680 sulfoxaflor M.845 I-697 sulfoxaflor M.846 I-698 sulfoxaflor M.847 I-775 sulfoxaflor M.848 I-776 sulfoxaflor M.849 I-793 sulfoxaflor M.850 I-794 sulfoxaflor M.851 I-871 sulfoxaflor M.852 I-872 sulfoxaflor M.853 I-877 sulfoxaflor M.854 I-878 sulfoxaflor M.855 I-2563 sulfoxaflor M.856 I-2564 sulfoxaflor M.857 I-2671 sulfoxaflor M.858 I-2672 sulfoxaflor M.859 I-1 afidopyropen M.860 I-2 afidopyropen M.861 I-13 afidopyropen M.862 I-14 afidopyropen M.863 I-673 afidopyropen M.864 I-674 afidopyropen M.865 I-679 afidopyropen M.866 I-680 afidopyropen M.867 I-697 afidopyropen M.868 I-698 afidopyropen M.869 I-775 afidopyropen M.870 I-776 afidopyropen M.871 I-793 afidopyropen M.872 I-794 afidopyropen M.873 I-871 afidopyropen M.874 I-872 afidopyropen M.875 I-877 afidopyropen M.876 I-878 afidopyropen M.877 I-2563 afidopyropen M.878 I-2564 afidopyropen M.879 I-2671 afidopyropen M.880 I-2672 afidopyropen

A further embodiment of the invention relates to mixtures of at least a compound of formula I with at least one compound B from the groups F.1 to F.11.

A preferred embodiment of the invention relates to mixtures of a compound of formula I with one compound B from the groups F.1 to F.11.

Binary mixtures of a compound of formula I and a compound B from the groups F.1 to F.11 are one preferred embodiment of the invention.

Ternary mixtures of a compound of formula I and two compounds B from the groups F.1 to F.11 are another preferred embodiment of the invention.

Ternary mixtures of a compound of formula I and a compound B from each of the groups A.1 to A.17 and F.1 to F.11 are another preferred embodiment of the invention.

A further embodiment of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.1a), preferably from azoxystrobin, pyraclostrobin, fluoxastrobin, picoxystrobin and trifloxystrobin.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group of the F.1b), preferably cyazofamid.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.1c), preferably from boscalid, fluopyram, fluxapyroxad, penthiopyrad, and sedaxane.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.1d), preferably selected from silthiofam and ametoctradin.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.2a), preferably from difenoconazole, epoxiconazole, fluquinconazole, ipconazole, prothioconazole, tebuconazole, triticonazole, and prochloraz.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.2b).

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.2c), preferably fenhexamid.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.3a), preferably from metalaxyl, and metalaxyl-M.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.3b).

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.4a), preferably from carbendazim, and thiophanate-methyl.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.4b).

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.5a), preferably selected from cyprodinil and pyrimethanil.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.5b).

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.6a), preferably iprodione.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.6b).

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.7a).

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.7b).

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.7c), preferably selected from benthiavalicarb and iprovalicarb.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.7d).

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.8a).

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.8b), preferably selected from thiram and mancozeb.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.8c), preferably chlorothalonil.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.8d).

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.9.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.10.

A further embodiment relates to mixtures of a compound of the formula I with at least one active compound B selected from the group F.11 of fungicides of unknown mode of action.

A particular group of embodiments of relates to mixtures of a compound of the formula I with at least one active compound B selected from the group consisting of azoxystrobin, fluoxastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, fluxapyroxad, benthiavalicarb, iprovalicarb, fenhexamid, boscalid, mancozeb, ametoctradin, metalalxyl-m, pyrimethanil, cyprodinil, carbendazim, iprodion, cyazofamid, prochloraz, chlorothalonil, penthiopyrad, difenoconazole, epoxiconazole, ipconazole, prothioconazole and tebuconazole.

Especially preferred are inventive mixtures wherein the compound B is azoxystrobin and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is fluoxastrobin and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is picoxystrobin and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is pyraclostrobin and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is trifloxystrobin and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is fluoxapyroxad and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is benthiavalicarb and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is iprovalicarb and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is fenhexamid and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is boscalid and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is mancozeb and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is ametoctradin and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is metalalxyl-m and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is pyrimethanil and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is cyprodinil and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is carbendazim and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is iprodion and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is cyazofamid and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is prochloraz and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is chlorothalonil and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is penthiopyrad and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is difenoconazole and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is epoxiconazole and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is ipconazole and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is prothioconazole and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

Especially preferred are inventive mixtures wherein the compound B is tebuconazole and the compound I of formula I is a compound of Table I, Table II, Table III, or Table IV.

The following table M-F represents preferred combinations of the active compounds I of formula I as defined in table I and the active compounds B of groups F.1 to F.11 in mixtures according to the invention:

TABLE M-F No. Comp. I Comp. B M.881 I-1 pyraclostrobin M.882 I-2 pyraclostrobin M.883 I-13 pyraclostrobin M.884 I-14 pyraclostrobin M.885 I-673 pyraclostrobin M.886 I-674 pyraclostrobin M.887 I-679 pyraclostrobin M.888 I-680 pyraclostrobin M.889 I-697 pyraclostrobin M.890 I-698 pyraclostrobin M.891 I-775 pyraclostrobin M.892 I-776 pyraclostrobin M.893 I-793 pyraclostrobin M.894 I-794 pyraclostrobin M.895 I-871 pyraclostrobin M.896 I-872 pyraclostrobin M.897 I-877 pyraclostrobin M.898 I-878 pyraclostrobin M.899 I-2563 pyraclostrobin M.900 I-2564 pyraclostrobin M.901 I-2671 pyraclostrobin M.902 I-2672 pyraclostrobin M.903 I-1 trifloxystrobin M.904 I-2 trifloxystrobin M.905 I-13 trifloxystrobin M.906 I-14 trifloxystrobin M.907 I-673 trifloxystrobin M.908 I-674 trifloxystrobin M.909 I-679 trifloxystrobin M.910 I-680 trifloxystrobin M.911 I-697 trifloxystrobin M.912 I-698 trifloxystrobin M.913 I-775 trifloxystrobin M.914 I-776 trifloxystrobin M.915 I-793 trifloxystrobin M.916 I-794 trifloxystrobin M.917 I-871 trifloxystrobin M.918 I-872 trifloxystrobin M.919 I-877 trifloxystrobin M.920 I-878 trifloxystrobin M.921 I-2563 trifloxystrobin M.922 I-2564 trifloxystrobin M.923 I-2671 trifloxystrobin M.924 I-2672 trifloxystrobin M.925 I-1 fluoxastrobin M.926 I-2 fluoxastrobin M.927 I-13 fluoxastrobin M.928 I-14 fluoxastrobin M.929 I-673 fluoxastrobin M.930 I-674 fluoxastrobin M.931 I-679 fluoxastrobin M.932 I-680 fluoxastrobin M.933 I-697 fluoxastrobin M.934 I-698 fluoxastrobin M.935 I-775 fluoxastrobin M.936 I-776 fluoxastrobin M.937 I-793 fluoxastrobin M.938 I-794 fluoxastrobin M.939 I-871 fluoxastrobin M.940 I-872 fluoxastrobin M.941 I-877 fluoxastrobin M.942 I-878 fluoxastrobin M.943 I-2563 fluoxastrobin M.944 I-2564 fluoxastrobin M.945 I-2671 fluoxastrobin M.946 I-2672 fluoxastrobin M.947 I-1 picoxystrobin M.948 I-2 picoxystrobin M.949 I-13 picoxystrobin M.950 I-14 picoxystrobin M.951 I-673 picoxystrobin M.952 I-674 picoxystrobin M.953 I-679 picoxystrobin M.954 I-680 picoxystrobin M.955 I-697 picoxystrobin M.956 I-698 picoxystrobin M.957 I-775 picoxystrobin M.958 I-776 picoxystrobin M.959 I-793 picoxystrobin M.960 I-794 picoxystrobin M.961 I-871 picoxystrobin M.962 I-872 picoxystrobin M.963 I-877 picoxystrobin M.964 I-878 picoxystrobin M.965 I-2563 picoxystrobin M.966 I-2564 picoxystrobin M.967 I-2671 picoxystrobin M.968 I-2672 picoxystrobin M.969 I-1 azoxystrobin M.970 I-2 azoxystrobin M.971 I-13 azoxystrobin M.972 I-14 azoxystrobin M.973 I-673 azoxystrobin M.974 I-674 azoxystrobin M.975 I-679 azoxystrobin M.976 I-680 azoxystrobin M.977 I-697 azoxystrobin M.978 I-698 azoxystrobin M.979 I-775 azoxystrobin M.980 I-776 azoxystrobin M.981 I-793 azoxystrobin M.982 I-794 azoxystrobin M.983 I-871 azoxystrobin M.984 I-872 azoxystrobin M.985 I-877 azoxystrobin M.986 I-878 azoxystrobin M.987 I-2563 azoxystrobin M.988 I-2564 azoxystrobin M.989 I-2671 azoxystrobin M.990 I-2672 azoxystrobin M.991 I-1 cyazofamid M.992 I-2 cyazofamid M.993 I-13 cyazofamid M.994 I-14 cyazofamid M.995 I-673 cyazofamid M.996 I-674 cyazofamid M.997 I-679 cyazofamid M.998 I-680 cyazofamid M.999 I-697 cyazofamid M.1000 I-698 cyazofamid M.1001 I-775 cyazofamid M.1002 I-776 cyazofamid M.1003 I-793 cyazofamid M.1004 I-794 cyazofamid M.1005 I-871 cyazofamid M.1006 I-872 cyazofamid M.1007 I-877 cyazofamid M.1008 I-878 cyazofamid M.1009 I-2563 cyazofamid M.1010 I-2564 cyazofamid M.1011 I-2671 cyazofamid M.1012 I-2672 cyazofamid M.1013 I-1 boscalid M.1014 I-2 boscalid M.1015 I-13 boscalid M.1016 I-14 boscalid M.1017 I-673 boscalid M.1018 I-674 boscalid M.1019 I-679 boscalid M.1020 I-680 boscalid M.1021 I-697 boscalid M.1022 I-698 boscalid M.1023 I-775 boscalid M.1024 I-776 boscalid M.1025 I-793 boscalid M.1026 I-794 boscalid M.1027 I-871 boscalid M.1028 I-872 boscalid M.1029 I-877 boscalid M.1030 I-878 boscalid M.1031 I-2563 boscalid M.1032 I-2564 boscalid M.1033 I-2671 boscalid M.1034 I-2672 boscalid M.1035 I-1 fluopyram M.1036 I-2 fluopyram M.1037 I-13 fluopyram M.1038 I-14 fluopyram M.1039 I-673 fluopyram M.1040 I-674 fluopyram M.1041 I-679 fluopyram M.1042 I-680 fluopyram M.1043 I-697 fluopyram M.1044 I-698 fluopyram M.1045 I-775 fluopyram M.1046 I-776 fluopyram M.1047 I-793 fluopyram M.1048 I-794 fluopyram M.1049 I-871 fluopyram M.1050 I-872 fluopyram M.1051 I-877 fluopyram M.1052 I-878 fluopyram M.1053 I-2563 fluopyram M.1054 I-2564 fluopyram M.1055 I-2671 fluopyram M.1056 I-2672 fluopyram M.1057 I-1 fluxapyroxad M.1058 I-2 fluxapyroxad M.1059 I-13 fluxapyroxad M.1060 I-14 fluxapyroxad M.1061 I-673 fluxapyroxad M.1062 I-674 fluxapyroxad M.1063 I-679 fluxapyroxad M.1064 I-680 fluxapyroxad M.1065 I-697 fluxapyroxad M.1066 I-698 fluxapyroxad M.1067 I-775 fluxapyroxad M.1068 I-776 fluxapyroxad M.1069 I-793 fluxapyroxad M.1070 I-794 fluxapyroxad M.1071 I-871 fluxapyroxad M.1072 I-872 fluxapyroxad M.1073 I-877 fluxapyroxad M.1074 I-878 fluxapyroxad M.1075 I-2563 fluxapyroxad M.1076 I-2564 fluxapyroxad M.1077 I-2671 fluxapyroxad M.1078 I-2672 fluxapyroxad M.1079 I-1 penthiopyrad M.1080 I-2 penthiopyrad M.1081 I-13 penthiopyrad M.1082 I-14 penthiopyrad M.1083 I-673 penthiopyrad M.1084 I-674 penthiopyrad M.1085 I-679 penthiopyrad M.1086 I-680 penthiopyrad M.1087 I-697 penthiopyrad M.1088 I-698 penthiopyrad M.1089 I-775 penthiopyrad M.1090 I-776 penthiopyrad M.1091 I-793 penthiopyrad M.1092 I-794 penthiopyrad M.1093 I-871 penthiopyrad M.1094 I-872 penthiopyrad M.1095 I-877 penthiopyrad M.1096 I-878 penthiopyrad M.1097 I-2563 penthiopyrad M.1098 I-2564 penthiopyrad M.1099 I-2671 penthiopyrad M.1100 I-2672 penthiopyrad M.1101 I-1 sedaxane M.1102 I-2 sedaxane M.1103 I-13 sedaxane M.1104 I-14 sedaxane M.1105 I-673 sedaxane M.1106 I-674 sedaxane M.1107 I-679 sedaxane M.1108 I-680 sedaxane M.1109 I-697 sedaxane M.1110 I-698 sedaxane M.1111 I-775 sedaxane M.1112 I-776 sedaxane M.1113 I-793 sedaxane M.1114 I-794 sedaxane M.1115 I-871 sedaxane M.1116 I-872 sedaxane M.1117 I-877 sedaxane M.1118 I-878 sedaxane M.1119 I-2563 sedaxane M.1120 I-2564 sedaxane M.1121 I-2671 sedaxane M.1122 I-2672 sedaxane M.1123 I-1 silthiofam M.1124 I-2 silthiofam M.1125 I-13 silthiofam M.1126 I-14 silthiofam M.1127 I-673 silthiofam M.1128 I-674 silthiofam M.1129 I-679 silthiofam M.1130 I-680 silthiofam M.1131 I-697 silthiofam M.1132 I-698 silthiofam M.1133 I-775 silthiofam M.1134 I-776 silthiofam M.1135 I-793 silthiofam M.1136 I-794 silthiofam M.1137 I-871 silthiofam M.1138 I-872 silthiofam M.1139 I-877 silthiofam M.1140 I-878 silthiofam M.1141 I-2563 silthiofam M.1142 I-2564 silthiofam M.1143 I-2671 silthiofam M.1144 I-2672 silthiofam M.1145 I-1 ametoctradin M.1146 I-2 ametoctradin M.1147 I-13 ametoctradin M.1148 I-14 ametoctradin M.1149 I-673 ametoctradin M.1150 I-674 ametoctradin M.1151 I-679 ametoctradin M.1152 I-680 ametoctradin M.1153 I-697 ametoctradin M.1154 I-698 ametoctradin M.1155 I-775 ametoctradin M.1156 I-776 ametoctradin M.1157 I-793 ametoctradin M.1158 I-794 ametoctradin M.1159 I-871 ametoctradin M.1160 I-872 ametoctradin M.1161 I-877 ametoctradin M.1162 I-878 ametoctradin M.1163 I-2563 ametoctradin M.1164 I-2564 ametoctradin M.1165 I-2671 ametoctradin M.1166 I-2672 ametoctradin M.1167 I-1 epoxiconazol M.1168 I-2 epoxiconazol M.1169 I-13 epoxiconazol M.1170 I-14 epoxiconazol M.1171 I-673 epoxiconazol M.1172 I-674 epoxiconazol M.1173 I-679 epoxiconazol M.1174 I-680 epoxiconazol M.1175 I-697 epoxiconazol M.1176 I-698 epoxiconazol M.1177 I-775 epoxiconazol M.1178 I-776 epoxiconazol M.1179 I-793 epoxiconazol M.1180 I-794 epoxiconazol M.1181 I-871 epoxiconazol M.1182 I-872 epoxiconazol M.1183 I-877 epoxiconazol M.1184 I-878 epoxiconazol M.1185 I-2563 epoxiconazol M.1186 I-2564 epoxiconazol M.1187 I-2671 epoxiconazol M.1188 I-2672 epoxiconazol M.1189 I-1 difenoconazol M.1190 I-2 difenoconazol M.1191 I-13 difenoconazol M.1192 I-14 difenoconazol M.1193 I-673 difenoconazol M.1194 I-674 difenoconazol M.1195 I-679 difenoconazol M.1196 I-680 difenoconazol M.1197 I-697 difenoconazol M.1198 I-698 difenoconazol M.1199 I-775 difenoconazol M.1200 I-776 difenoconazol M.1201 I-793 difenoconazol M.1202 I-794 difenoconazol M.1203 I-871 difenoconazol M.1204 I-872 difenoconazol M.1205 I-877 difenoconazol M.1206 I-878 difenoconazol M.1207 I-2563 difenoconazol M.1208 I-2564 difenoconazol M.1209 I-2671 difenoconazol M.1210 I-2672 difenoconazol M.1211 I-1 ipconazole M.1212 I-2 ipconazole M.1213 I-13 ipconazole M.1214 I-14 ipconazole M.1215 I-673 ipconazole M.1216 I-674 ipconazole M.1217 I-679 ipconazole M.1218 I-680 ipconazole M.1219 I-697 ipconazole M.1220 I-698 ipconazole M.1221 I-775 ipconazole M.1222 I-776 ipconazole M.1223 I-793 ipconazole M.1224 I-794 ipconazole M.1225 I-871 ipconazole M.1226 I-872 ipconazole M.1227 I-877 ipconazole M.1228 I-878 ipconazole M.1229 I-2563 ipconazole M.1230 I-2564 ipconazole M.1231 I-2671 ipconazole M.1232 I-2672 ipconazole M.1233 I-1 prothioconazole M.1234 I-2 prothioconazole M.1235 I-13 prothioconazole M.1236 I-14 prothioconazole M.1237 I-673 prothioconazole M.1238 I-674 prothioconazole M.1239 I-679 prothioconazole M.1240 I-680 prothioconazole M.1241 I-697 prothioconazole M.1242 I-698 prothioconazole M.1243 I-775 prothioconazole M.1244 I-776 prothioconazole M.1245 I-793 prothioconazole M.1246 I-794 prothioconazole M.1247 I-871 prothioconazole M.1248 I-872 prothioconazole M.1249 I-877 prothioconazole M.1250 I-878 prothioconazole M.1251 I-2563 prothioconazole M.1252 I-2564 prothioconazole M.1253 I-2671 prothioconazole M.1254 I-2672 prothioconazole M.1255 I-1 tebuconazole M.1256 I-2 tebuconazole M.1257 I-13 tebuconazole M.1258 I-14 tebuconazole M.1259 I-673 tebuconazole M.1260 I-674 tebuconazole M.1261 I-679 tebuconazole M.1262 I-680 tebuconazole M.1263 I-697 tebuconazole M.1264 I-698 tebuconazole M.1265 I-775 tebuconazole M.1266 I-776 tebuconazole M.1267 I-793 tebuconazole M.1268 I-794 tebuconazole M.1269 I-871 tebuconazole M.1270 I-872 tebuconazole M.1271 I-877 tebuconazole M.1272 I-878 tebuconazole M.1273 I-2563 tebuconazole M.1274 I-2564 tebuconazole M.1275 I-2671 tebuconazole M.1276 I-2672 tebuconazole M.1277 I-1 fluquinconazole M.1278 I-2 fluquinconazole M.1279 I-13 fluquinconazole M.1280 I-14 fluquinconazole M.1281 I-673 fluquinconazole M.1282 I-674 fluquinconazole M.1283 I-679 fluquinconazole M.1284 I-680 fluquinconazole M.1285 I-697 fluquinconazole M.1286 I-698 fluquinconazole M.1287 I-775 fluquinconazole M.1288 I-776 fluquinconazole M.1289 I-793 fluquinconazole M.1290 I-794 fluquinconazole M.1291 I-871 fluquinconazole M.1292 I-872 fluquinconazole M.1293 I-877 fluquinconazole M.1294 I-878 fluquinconazole M.1295 I-2563 fluquinconazole M.1296 I-2564 fluquinconazole M.1297 I-2671 fluquinconazole M.1298 I-2672 fluquinconazole M.1299 I-1 triticonazole M.1300 I-2 triticonazole M.1301 I-13 triticonazole M.1302 I-14 triticonazole M.1303 I-673 triticonazole M.1304 I-674 triticonazole M.1305 I-679 triticonazole M.1306 I-680 triticonazole M.1307 I-697 triticonazole M.1308 I-698 triticonazole M.1309 I-775 triticonazole M.1310 I-776 triticonazole M.1311 I-793 triticonazole M.1312 I-794 triticonazole M.1313 I-871 triticonazole M.1314 I-872 triticonazole M.1315 I-877 triticonazole M.1316 I-878 triticonazole M.1317 I-2563 triticonazole M.1318 I-2564 triticonazole M.1319 I-2671 triticonazole M.1320 I-2672 triticonazole M.1321 I-1 prochloraz M.1322 I-2 prochloraz M.1323 I-13 prochloraz M.1324 I-14 prochloraz M.1325 I-673 prochloraz M.1326 I-674 prochloraz M.1327 I-679 prochloraz M.1328 I-680 prochloraz M.1329 I-697 prochloraz M.1330 I-698 prochloraz M.1331 I-775 prochloraz M.1332 I-776 prochloraz M.1333 I-793 prochloraz M.1334 I-794 prochloraz M.1335 I-871 prochloraz M.1336 I-872 prochloraz M.1337 I-877 prochloraz M.1338 I-878 prochloraz M.1339 I-2563 prochloraz M.1340 I-2564 prochloraz M.1341 I-2671 prochloraz M.1342 I-2672 prochloraz M.1343 I-1 fenhexamid M.1344 I-2 fenhexamid M.1345 I-13 fenhexamid M.1346 I-14 fenhexamid M.1347 I-673 fenhexamid M.1348 I-674 fenhexamid M.1349 I-679 fenhexamid M.1350 I-680 fenhexamid M.1351 I-697 fenhexamid M.1352 I-698 fenhexamid M.1353 I-775 fenhexamid M.1354 I-776 fenhexamid M.1355 I-793 fenhexamid M.1356 I-794 fenhexamid M.1357 I-871 fenhexamid M.1358 I-872 fenhexamid M.1359 I-877 fenhexamid M.1360 I-878 fenhexamid M.1361 I-2563 fenhexamid M.1362 I-2564 fenhexamid M.1363 I-2671 fenhexamid M.1364 I-2672 fenhexamid M.1365 I-1 metalaxyl M.1366 I-2 metalaxyl M.1367 I-13 metalaxyl M.1368 I-14 metalaxyl M.1369 I-673 metalaxyl M.1370 I-674 metalaxyl M.1371 I-679 metalaxyl M.1372 I-680 metalaxyl M.1373 I-697 metalaxyl M.1374 I-698 metalaxyl M.1375 I-775 metalaxyl M.1376 I-776 metalaxyl M.1377 I-793 metalaxyl M.1378 I-794 metalaxyl M.1379 I-871 metalaxyl M.1380 I-872 metalaxyl M.1381 I-877 metalaxyl M.1382 I-878 metalaxyl M.1383 I-2563 metalaxyl M.1384 I-2564 metalaxyl M.1385 I-2671 metalaxyl M.1386 I-2672 metalaxyl M.1387 I-1 metalaxyl-M M.1388 I-2 metalaxyl-M M.1389 I-13 metalaxyl-M M.1390 I-14 metalaxyl-M M.1391 I-673 metalaxyl-M M.1392 I-674 metalaxyl-M M.1393 I-679 metalaxyl-M M.1394 I-680 metalaxyl-M M.1395 I-697 metalaxyl-M M.1396 I-698 metalaxyl-M M.1397 I-775 metalaxyl-M M.1398 I-776 metalaxyl-M M.1399 I-793 metalaxyl-M M.1400 I-794 metalaxyl-M M.1401 I-871 metalaxyl-M M.1402 I-872 metalaxyl-M M.1403 I-877 metalaxyl-M M.1404 I-878 metalaxyl-M M.1405 I-2563 metalaxyl-M M.1406 I-2564 metalaxyl-M M.1407 I-2671 metalaxyl-M M.1408 I-2672 metalaxyl-M M.1409 I-1 carbendazim M.1410 I-2 carbendazim M.1411 I-13 carbendazim M.1412 I-14 carbendazim M.1413 I-673 carbendazim M.1414 I-674 carbendazim M.1415 I-679 carbendazim M.1416 I-680 carbendazim M.1417 I-697 carbendazim M.1418 I-698 carbendazim M.1419 I-775 carbendazim M.1420 I-776 carbendazim M.1421 I-793 carbendazim M.1422 I-794 carbendazim M.1423 I-871 carbendazim M.1424 I-872 carbendazim M.1425 I-877 carbendazim M.1426 I-878 carbendazim M.1427 I-2563 carbendazim M.1428 I-2564 carbendazim M.1429 I-2671 carbendazim M.1430 I-2672 carbendazim M.1431 I-1 thiophanate-methyl M.1432 I-2 thiophanate-methyl M.1433 I-13 thiophanate-methyl M.1434 I-14 thiophanate-methyl M.1435 I-673 thiophanate-methyl M.1436 I-674 thiophanate-methyl M.1437 I-679 thiophanate-methyl M.1438 I-680 thiophanate-methyl M.1439 I-697 thiophanate-methyl M.1440 I-698 thiophanate-methyl M.1441 I-775 thiophanate-methyl M.1442 I-776 thiophanate-methyl M.1443 I-793 thiophanate-methyl M.1444 I-794 thiophanate-methyl M.1445 I-871 thiophanate-methyl M.1446 I-872 thiophanate-methyl M.1447 I-877 thiophanate-methyl M.1448 I-878 thiophanate-methyl M.1449 I-2563 thiophanate-methyl M.1450 I-2564 thiophanate-methyl M.1451 I-2671 thiophanate-methyl M.1452 I-2672 thiophanate-methyl M.1453 I-1 cyprodinil M.1454 I-2 cyprodinil M.1455 I-13 cyprodinil M.1456 I-14 cyprodinil M.1457 I-673 cyprodinil M.1458 I-674 cyprodinil M.1459 I-679 cyprodinil M.1460 I-680 cyprodinil M.1461 I-697 cyprodinil M.1462 I-698 cyprodinil M.1463 I-775 cyprodinil M.1464 I-776 cyprodinil M.1465 I-793 cyprodinil M.1466 I-794 cyprodinil M.1467 I-871 cyprodinil M.1468 I-872 cyprodinil M.1469 I-877 cyprodinil M.1470 I-878 cyprodinil M.1471 I-2563 cyprodinil M.1472 I-2564 cyprodinil M.1473 I-2671 cyprodinil M.1474 I-2672 cyprodinil M.1475 I-1 pyrimethanil M.1476 I-2 pyrimethanil M.1477 I-13 pyrimethanil M.1478 I-14 pyrimethanil M.1479 I-673 pyrimethanil M.1480 I-674 pyrimethanil M.1481 I-679 pyrimethanil M.1482 I-680 pyrimethanil M.1483 I-697 pyrimethanil M.1484 I-698 pyrimethanil M.1485 I-775 pyrimethanil M.1486 I-776 pyrimethanil M.1487 I-793 pyrimethanil M.1488 I-794 pyrimethanil M.1489 I-871 pyrimethanil M.1490 I-872 pyrimethanil M.1491 I-877 pyrimethanil M.1492 I-878 pyrimethanil M.1493 I-2563 pyrimethanil M.1494 I-2564 pyrimethanil M.1495 I-2671 pyrimethanil M.1496 I-2672 pyrimethanil M.1497 I-1 iprodione M.1498 I-2 iprodione M.1499 I-13 iprodione M.1500 I-14 iprodione M.1501 I-673 iprodione M.1502 I-674 iprodione M.1503 I-679 iprodione M.1504 I-680 iprodione M.1505 I-697 iprodione M.1506 I-698 iprodione M.1507 I-775 iprodione M.1508 I-776 iprodione M.1509 I-793 iprodione M.1510 I-794 iprodione M.1511 I-871 iprodione M.1512 I-872 iprodione M.1513 I-877 iprodione M.1514 I-878 iprodione M.1515 I-2563 iprodione M.1516 I-2564 iprodione M.1517 I-2671 iprodione M.1518 I-2672 iprodione M.1519 I-1 benthiavalicarb M.1520 I-2 benthiavalicarb M.1521 I-13 benthiavalicarb M.1522 I-14 benthiavalicarb M.1523 I-673 benthiavalicarb M.1524 I-674 benthiavalicarb M.1525 I-679 benthiavalicarb M.1526 I-680 benthiavalicarb M.1527 I-697 benthiavalicarb M.1528 I-698 benthiavalicarb M.1529 I-775 benthiavalicarb M.1530 I-776 benthiavalicarb M.1531 I-793 benthiavalicarb M.1532 I-794 benthiavalicarb M.1533 I-871 benthiavalicarb M.1534 I-872 benthiavalicarb M.1535 I-877 benthiavalicarb M.1536 I-878 benthiavalicarb M.1537 I-2563 benthiavalicarb M.1538 I-2564 benthiavalicarb M.1539 I-2671 benthiavalicarb M.1540 I-2672 benthiavalicarb M.1541 I-1 iprovalicarb M.1542 I-2 iprovalicarb M.1543 I-13 iprovalicarb M.1544 I-14 iprovalicarb M.1545 I-673 iprovalicarb M.1546 I-674 iprovalicarb M.1547 I-679 iprovalicarb M.1548 I-680 iprovalicarb M.1549 I-697 iprovalicarb M.1550 I-698 iprovalicarb M.1551 I-775 iprovalicarb M.1552 I-776 iprovalicarb M.1553 I-793 iprovalicarb M.1554 I-794 iprovalicarb M.1555 I-871 iprovalicarb M.1556 I-872 iprovalicarb M.1557 I-877 iprovalicarb M.1558 I-878 iprovalicarb M.1559 I-2563 iprovalicarb M.1560 I-2564 iprovalicarb M.1561 I-2671 iprovalicarb M.1562 I-2672 iprovalicarb M.1563 I-1 thiram M.1564 I-2 thiram M.1565 I-13 thiram M.1566 I-14 thiram M.1567 I-673 thiram M.1568 I-674 thiram M.1569 I-679 thiram M.1570 I-680 thiram M.1571 I-697 thiram M.1572 I-698 thiram M.1573 I-775 thiram M.1574 I-776 thiram M.1575 I-793 thiram M.1576 I-794 thiram M.1577 I-871 thiram M.1578 I-872 thiram M.1579 I-877 thiram M.1580 I-878 thiram M.1581 I-2563 thiram M.1582 I-2564 thiram M.1583 I-2671 thiram M.1584 I-2672 thiram M.1585 I-1 mancozeb M.1586 I-2 mancozeb M.1587 I-13 mancozeb M.1588 I-14 mancozeb M.1589 I-673 mancozeb M.1590 I-674 mancozeb M.1591 I-679 mancozeb M.1592 I-680 mancozeb M.1593 I-697 mancozeb M.1594 I-698 mancozeb M.1595 I-775 mancozeb M.1596 I-776 mancozeb M.1597 I-793 mancozeb M.1598 I-794 mancozeb M.1599 I-871 mancozeb M.1600 I-872 mancozeb M.1601 I-877 mancozeb M.1602 I-878 mancozeb M.1603 I-2563 mancozeb M.1604 I-2564 mancozeb M.1605 I-2671 mancozeb M.1606 I-2672 mancozeb M.1607 I-1 chlorothalonil M.1608 I-2 chlorothalonil M.1609 I-13 chlorothalonil M.1610 I-14 chlorothalonil M.1611 I-673 chlorothalonil M.1612 I-674 chlorothalonil M.1613 I-679 chlorothalonil M.1614 I-680 chlorothalonil M.1615 I-697 chlorothalonil M.1616 I-698 chlorothalonil M.1617 I-775 chlorothalonil M.1618 I-776 chlorothalonil M.1619 I-793 chlorothalonil M.1620 I-794 chlorothalonil M.1621 I-871 chlorothalonil M.1622 I-872 chlorothalonil M.1623 I-877 chlorothalonil M.1624 I-878 chlorothalonil M.1625 I-2563 chlorothalonil M.1626 I-2564 chlorothalonil M.1627 I-2671 chlorothalonil M.1628 I-2672 chlorothalonil

The mixtures of the present invention have excellent activity against a broad spectrum of phytopathogenic fungi and animal pests.

The inventive compounds and the mixtures of the present invention have excellent activity against a broad spectrum of animal pests.

They are in particular suitable for efficiently controlling invertebrate pests. Particular, they are suitable for efficiently controlling arthropodal pests such as arachnids, myriapedes and insects as well as nematodes.

In particular, they are suitable for controlling insect pests, such as insects from the order of lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Grapholitha molesta, Heliothis armigera, Heliothis virescens, Heliothis zea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersicella, Lambdina fiscellaria, Laphygma exigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletis blancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar, Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestra brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudoplusia includens Rhyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis;

beetles (Coleoptera), for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Ctenicera ssp., Diabrotica longicornis, Diabrotica semipunctata, Diabrotica 12-punctata Diabrotica speciosa, Diabrotica virgifera, Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis, Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Otiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria;

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nignpalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Della antique, Delia coarctata, Della platura, Della radicum, Dermatobia hominis, Fannia canicularis, Geomyza Tripunctata, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hylemyia platura, Hypoderma lineata, Leptoconops torrens, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia titillanus, Mayetiola destructor, Musca autumnalis, Musca domestica, Muscina stabulans, Oestrus ovis, Opomyza florum, Oscinella frit, Pegomya hysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Phlebotomus argentipes, Psorophora columbiae, Psila rosae, Psorophora discolor, Prosimulium mixtum, Rhagoletis cerasi, Rhagoletis pomonella, Sarcophaga haemorrhoidalis, Sarcophaga spp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus similis, Tipula oleracea, and Tipula paludosa;

thrips (Thysanoptera), e.g. Dichromothrips corbetti, Dichromothrips ssp., Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,

termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Reticulitermes santonensis, Reticulitermes grassei, Termes natalensis, and Coptotermes formosanus;

cockroaches (Blattaria-Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalls;

bugs, aphids, leafhoppers, whiteflies, scale insects, cicadas (Hemiptera), e.g. Acrostemum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara viridula, Piesma quadrata, Solubea insularis, Thyanta perditor, Acyrthosiphon onothychis, Adelges laricis, Aphidula nasturtii, Aphlis fabae, Aphis forbesi, Aphis pomi, Aphlis gossypii, Aphis grossulariae, Aphlis schneideri, Aphlis spiraecola, Aphlis sambuci, Acyrthosiphon pisum, Aulacorthum solani, Bemisia argentifolii, Brachycaudus cardui, Brachycaudus Brachycaudus persicae, Brachycaudus prunicola, Brevicoryne brassicae, Capitophorus horni, Cerosipha gossypii, Chaetosiphon fragaefolii, Cryptomyzus ribis, Dreyfusia nordmannianae, Dreyfusia piceae, Dysaphlis radicola, Dysaulacorthum pseudosolani, Dysaphis plantaginea, Dysaphlis pyri, Empoasca fabae, Hyalopterus pruni, Hyperomyzus lactucae, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megoura viciae, Melanaphlis pyrarius, Metopolophium dirhodum, Myzus persicae, Myzus ascalonicus, Myzus cerasi, Myzus varians, Nasonovia ribis-nigri, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus, Rhopalosiphum maidis, Rhopalosiphum padi, Rhopalosiphum insertum, Sappaphis mala, Sappaphis mali, Schizaphis graminum, Schizoneura lanuginosa, Sitobion avenae, Trialeurodes vaporariorum, Toxoptera aurantiiand, Viteus vitifolii, Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., and Arilus critatus;

ants, bees, wasps, sawflies (Hymenoptera), e.g. Athalia rosae, Atta cephalotes, Atta capiguara, Atta cephalotes, Atta laevigata, Atta robusta, Atta sexdens, Atta texana, Crematogaster spp., Hoplocampa minuta, Hoplocampa testudinea, Lasius niger, Monomorium pharaonis, Solenopsis geminata, Solenopsis invicta, Solenopsis richteri, Solenopsis xyloni, Pogonomyrmex barbatus, Pogonomyrmex californicus, Pheidole megacephala, Dasymutilla occidentalis, Bombus spp., Vespula squamosa, Paravespula vulgaris, Paravespula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile;

crickets, grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, and Locustana pardalina;

arachnoidea, such as arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Ambryomma maculatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Dermacentor andersoni, Dermacentor variabilis, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Ornithodorus moubata, Ornithodorus hermsi, Ornithodorus turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus sanguineus, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and Oligonychus pratensis; Araneida, e.g. Latrodectus mactans, and Loxosceles reclusa;

fleas (Siphonaptera), e.g. Ctenocephalides felis, Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga penetrans, and Nosopsyllus fasciatus,

silverfish, firebrat (Thysanura), e.g. Lepisma saccharina and Thermobia domestica,

centipedes (Chilopoda), e.g. Scutigera coleoptrata,

millipedes (Diplopoda), e.g. Narceus spp.,

earwigs (Dermaptera), e.g. forficula auricularia,

lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus.

Collembola (springtails), e.g. Onychiurus ssp.

They are also suitable for controlling nematodes: plant parasitic nematodes such as root knot nematodes, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst-forming nematodes, Globodera rostochiensis and other Globodera species; Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Belonolaimus longicaudatus and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, Mesocriconema species; Stem and bulb nematodes, Ditylenchus destructor, Ditylenchus dipsaci and other Ditylenchus species; Awl nematodes, Dolichodorus species; Spiral nematodes, Heliocotylenchus multicinctus and other Helicotylenchus species; Sheath and sheathoid nematodes, Hemicycliophora species and Hemicriconemoides species; Hirshmanniella species; Lance nematodes, Hoploaimus species; false rootknot nematodes, Nacobbus species; Needle nematodes, Longidorus elongatus and other Longidorus species; Lesion nematodes, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus, Pratylenchus goodeyi and other Pratylenchus species; Burrowing nematodes, Radopholus similis and other Radopholus species; Reniform nematodes, Rotylenchus robustus and other Rotylenchus species; Scutellonema species; Stubby root nematodes, Trichodorus primitivus and other Trichodorus species, Paratrichodorus species; Stunt nematodes, Tylenchorhynchus claytoni, Tylenchorhynchus dubius and other Tylenchorhynchus species; Citrus nematodes, Tylenchulus species; Dagger nematodes, Xiphinema species; and other plant parasitic nematode species.

They are also useful for controlling arachnids (Arachnoidea), such as acarians (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubata, Otobius megnini, Dermanyssus gallinae, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, and Eriophyidae spp. such as Aculus schlechtendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetranychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panonychus citri, and oligonychus pratensis.

The mixtures of the present invention have excellent activity against a broad spectrum of phytopathogenic fungi Ascomycetes, Basidiomycetes, Deuteromycetes and Peronosporomycetes (syn. Oomycetes). Some of them are systemically effective and can be employed in crop protection as foliar fungicides, as fungicides for seed dressing and as soil fungicides. They can also be used for treating seed.

They are particularly important in the control of a multitude of fungi on various cultivated plants, such as wheat, rye, barley, oats, rice, corn, lawns, bananas, cotton, soybean, coffee, sugar cane, grapevines, fruits and ornamental plants, and vegetables such as cucumbers, beans, tomatoes, potatoes and cucurbits, and on the seeds of these plants.

They are especially suitable for controlling the following plant diseases:

-   -   Alternaria species on vegetables, oilseed rape, sugar beet and         fruit and rice, for example, A. solani or A. alternata on         potatoes and tomatoes;     -   Aphanomyces species on sugar beet and vegetables;     -   Ascochyta species on cereals and vegetables;     -   Bipolaris and Drechslera species on corn, cereals, rice and         lawns, for example, D. maydis on corn;     -   Blumeria graminis (powdery mildew) on cereals;     -   Botrytis cinerea (gray mold) on strawberries, vegetables,         flowers and grapevines;     -   Bremia lactucae on lettuce;     -   Cercospora species on corn, soybeans, rice and sugar beet;     -   Cochliobolus species on corn, cereals, rice, for example         Cochliobolus sativus on cereals, Cochliobolus milyabeanus on         rice;     -   Colletotricum species on soybeans and cotton;     -   Drechslera species, Pyrenophora species on corn, cereals, rice         and lawns, for example, D. teres on barley or D.         tritici-repentis on wheat;     -   Esca on grapevines, caused by Phaeoacremonium chlamydosporium,         Ph. Aleophilum and Formitipora punctata (syn. Phellinus         punctatus);     -   Exserohilum species on corn;     -   Erysiphe cichoracearum and Sphaerotheca fuliginea on cucumbers;     -   Fusarium and Verticillium species on various plants, for         example, F. graminearum or F. culmorum on cereals or F.         oxysporum on a multitude of plants, such as, for example,         tomatoes;     -   Gaeumanomyces graminis on cereals;     -   Gibberella species on cereals and rice (for example Gibberella         fujikuroi on rice);     -   Grainstaining complex on rice;     -   Helminthosporium species on corn and rice;     -   Michrodochium nivale on cereals;     -   Mycosphaerella species on cereals, bananas and peanuts, for         example, M. graminicola on wheat or M. fijiensis on bananas;     -   Peronospora species on cabbage and bulbous plants, for         example, P. brassicae on cabbage or P. destructor on onions;     -   Phakopsara pachyrhizi and Phakopsara meibomiae on soybeans;     -   Phomopsis species on soybeans and sunflowers;     -   Phytophthora infestans on potatoes and tomatoes;     -   Phytophthora species on various plants, for example, P. capsici         on bell pepper;     -   Plasmopara viticola on grapevines;     -   Podosphaera leucotricha on apples;     -   Pseudocercosporella herpotrichoides on cereals;     -   Pseudoperonospora on various plants, for example, P. cubensis on         cucumber or P. humili on hops;     -   Puccinia species on various plants, for example, P.         triticina, P. striformins, P. hordei or P. graminis on cereals         or P. asparagi on asparagus;     -   Pyricularia olyzae, Corticium sasakil, Sarocladium olyzae, S.         attenuatum, Entyloma olyzae on rice;     -   Pyricularia grisea on lawns and cereals;     -   Pythium spp. on lawns, rice, corn, cotton, oilseed rape,         sunflowers, sugar beet, vegetables and other plants, for         example, P. ultiumum on various plants, P. aphanidermatum on         lawns;     -   Rhizoctonia species on cotton, rice, potatoes, lawns, corn,         oilseed rape, sugar beet, vegetables and on various plants, for         example, R. solani on beet and various plants;     -   Rhynchosporium secalls on barley, rye and triticale;     -   Sclerotinia species on oilseed rape and sunflowers;     -   Septoria tritici and Stagonospora nodorum on wheat;     -   Erysiphe (syn. Uncinula) necator on grapevines;     -   Setospaeria species on corn and lawns;     -   Sphacelotheca reilinia on corn;     -   Thievaliopsis species on soybeans and cotton;     -   Tilletia species on cereals;     -   Ustilago species on cereals, corn and sugar cane, for         example, U. maydis on corn;     -   Venturia species (scab) on apples and pears, for example, V.         inaequalis on apples.

The mixtures according to the invention are also suitable for controlling harmful fungi in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products. In the protection of wood, particular attention is paid to the following harmful fungi: Ascomycetes, such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes, such as Coniophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Deuteromycetes, such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternana spp., Paecilomyces spp. and Zygomycetes, such as Mucor spp., additionally in the protection of materials the following yeasts: Candida spp. and Saccharomyces cerevisae.

Moreover, the inventive mixtures are especially useful for the control of Lepidoptera, Coleoptera, Diptera, Thysanoptera and Hemiptera.

In particular the inventive mixtures are useful for the control of Thysanoptera and Hemiptera, especially Hemiptera.

The mixtures according to the present invention can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules. The use form depends on the particular intended purpose; in each case, it should ensure a fine and even distribution of the compounds according to the invention.

The formulations are prepared in a known manner (see e.g. for review U.S. Pat. No. 3,060,084, EP-A 707 445 (for liquid concentrates), Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, 147-48, Perry's Chemical Engineers Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and et seq. WO 91/13546, U.S. Pat. No. 4,172,714, U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442, U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701, U.S. Pat. No. 5,208,030, GB 2,095,558, U.S. Pat. No. 3,299,566, Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989 and Mollet, H., Grubemann, A., Formulation technology, Wiley VCH Verlag GmbH, Weinheim (Germany), 2001, 2. D. A. Knowles, Chemistry and Technology of Agrochemical Formulations, Kluwer Academic Publishers, Dordrecht, 1998 (ISBN 0-7514-0443-8), for example by extending the active corn-pound with auxiliaries suitable for the formulation of agrochemicals, such as solvents and/or carriers, if desired emulsifiers, surfactants and dispersants, preservatives, antifoaming agents, anti-freezing agents, for seed treatment formulation also optionally gelling agents.

Examples of suitable solvents are water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP(N-methyl-pyrrolidone), NOP (N-octyl-pyrrolidone), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used.

Suitable emulsifiers are nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates).

Examples of dispersants are lignin-sulfite waste liquors and methylcellulose.

Suitable surfactants used are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalene-sulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl polyglycol ether, tri-stearylphenyl polyglycol ether, alkylaryl polyether alcohols, alcohol and fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol ether acetal, sorbitol esters, lignosulfite waste liquors and methylcellulose.

Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water.

Also anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bactericides such as can be added to the formulation.

Suitable antifoaming agents are for example antifoaming agents based on silicon or magnesium stearate.

A suitable preservative is e.g. dichlorophen.

An example of a gelling agent is carrageen (Satiagel®)

Powders, materials for spreading and dustable products can be prepared by mixing or con-comitantly grinding the active substances with a solid carrier.

Granules, for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers.

Examples of solid carriers are mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.

In general, the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compounds. In this case, the active compounds are employed in a purity of from 90% to 100% by weight, preferably 95% to 100% by weight (according to NMR spectrum).

For seed treatment purposes, respective formulations can be diluted 2-10 fold leading to concentrations in the ready to use preparations of 0.01 to 60% by weight active compounds by weight, preferably 0.1 to 40% by weight.

The term “seed treatment” comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.

The mixtures of the present invention can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomizing, dusting, spreading or pouring. The use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of the active compounds according to the invention.

Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water. To prepare emulsions, pastes or oil dispersions, the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier. However, it is also possible to prepare concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil, and such concentrates are suitable for dilution with water.

The active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1% per weight.

The active compound(s) may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply the active compound without additives.

The following are examples of formulations:

1. Products for dilution with water for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.

A) Water-soluble concentrates (SL, LS)

10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active compound(s) dissolve(s) upon dilution with water, whereby a formulation with 10% (w/w) of active compound(s) is obtained.

B) Dispersible concentrates (DC)

20 parts by weight of the active compound(s) are dissolved in 70 parts by weight of cyclohexanone with addition of 10 parts by weight of a dispersant, for example polyvinylpyrrolidone. Dilution with water gives a dispersion, whereby a formulation with 20% (w/w) of active compound(s) is obtained.

C) Emulsifiable concentrates (EC)

15 parts by weight of the active compound(s) are dissolved in 7 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution with water gives an emulsion, whereby a formulation with 15% (w/w) of active compound(s) is obtained.

D) Emulsions (EW, EO, ES)

25 parts by weight of the active compound(s) are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). This mixture is introduced into 30 parts by weight of water by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w) of active compound(s) is obtained.

E) Suspensions (SC, OD, FS)

In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants, wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the active compound(s), whereby a formulation with 20% (w/w) of active compound(s) is obtained.

F) Water-dispersible granules and water-soluble granules (WG, SG)

50 parts by weight of the active compound(s) are ground finely with addition of 50 parts by weight of dispersants and wetters and made as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 50% (w/w) of active compound(s) is obtained.

G) Water-dispersible powders and water-soluble powders (WP, SP, SS, WS)

75 parts by weight of the active compound(s) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 75% (w/w) of active compound(s) is obtained.

H) Gel-Formulation (GF)

In an agitated ball mill, 20 parts by weight of the active compound(s) are comminuted with addition of 10 parts by weight of dispersants, 1 part by weight of gelling agent wetters and 70 parts by weight of water or of an organic solvent to give a fine active compound(s) suspension. Dilution with water gives a stable suspension of the active compound(s), whereby a formulation with 20% (w/w) of active compound(s) is obtained.

2. Products to be applied undiluted for foliar applications. For seed treatment purposes, such products may be applied to the seed diluted or undiluted.

I) Dustable powders (DP, DS)

5 parts by weight of the active compound(s) are ground finely and mixed intimately with 95 parts by weight of finely divided kaolin. This gives a dustable product having 5% (w/w) of active compound(s).

J) Granules (GR, FG, GG, MG)

0.5 part by weight of the active compound(s) is ground finely and associated with 95.5 parts by weight of carriers, whereby a formulation with 0.5% (w/w) of active compound(s) is obtained. Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted for foliar use.

K) ULV solutions (UL)

10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of an organic solvent, for example xylene. This gives a product having 10% (w/w) of active compound(s), which is applied undiluted for foliar use.

Various types of oils, wetters, adjuvants, herbicides, fungicides, other pesticides, or bactericides may be added to the active ingredients, if appropriate just immediately prior to use (tank mix). These agents usually are admixed with the agents according to the invention in a weight ratio of 1:10 to 10:1.

The compounds I and the one or more compound(s) B can be applied simultaneously, that is jointly or separately, or in succession, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.

The compounds of the present invention, the compositions comprising them or the mixtures of the present invention are employed as such or in form of compositions by treating the insects, the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from insecticidal attack with a pesticidally effective amount of the active compounds. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the insects.

The present invention also includes a method of combating animal pests and harmful fungi which comprises contacting the fungi and/or animal pests, their habit, breeding ground, food supply, cultivated plants, seed, soil, area, material or environment in which the animal pests are growing or may grow, or the materials, plants, seeds, soils, surfaces or spaces to be protected from animal attack or infestation with a pesticidally effective amount of a mixture according to the present invention or a compound of the invention. The compounds of the present invention, compositions comprising them, the inventive mixtures or compositions of these mixtures can also be employed for protecting plants from attack or infestation by invertebrate pests such as insects, acarids or nematodes comprising contacting a plant, or soil or water in which the plant is growing.

The pyrazole compound A selected from compounds I and the one or more compound(s) B are usually applied in a weight ratio of from 500:1 to 1:100, preferably from 20:1 to 1:50, in particular from 5:1 to 1:20.

In ternary mixtures the pyrazole compound A selected from compounds I compounds I and B are usually present in ratio ranges of from 500:1:1, to 500:100:1 to 500:100:1 to 1:100:100 to 1:100:1 to 1:1:100.

Depending on the desired effect, the application rates of the mixtures according to the invention are from 5 g/ha to 2000 g/ha, preferably from 50 to 1500 g/ha, in particular from 50 to 750 g/ha.

The compounds according to the present invention and the mixtures according to the invention are effective through both contact and ingestion.

According to a preferred embodiment of the invention, the mixtures according to the present invention are employed via soil application. According to a further preferred embodiment of the invention, the compounds according to the present invention are employed via soil application. Soil application is especially favorable for use against ants, termites, crickets, or cockroaches.

According to another preferred embodiment of the invention, for use against non crop pests such as ants, termites, wasps, flies, mosquitoes, crickets, locusts, or cockroaches the mixtures according to the present invention or the compounds of the present invention are prepared into a bait preparation. The compounds according to the invention may also be applied against said non-crop pests.

The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel).

Another aspect of the present invention is when preparing the mixtures, it is preferred to employ the pure active compounds I and B, to which further active compounds, e.g. against harmful fungi or having herbicidal activity, or growth-regulating agents or fertilizers can be added.

Compositions comprising an inventive compound of the formula I may further contain other active ingredients than those listed above. Compositions of this invention may further contain other active ingredients than those listed above. For example fungicides, herbicides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators and safeners. These additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix). For example, the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.

The mixtures according to the invention or compositions comprising the inventive compound I can be applied to any and all developmental stages, such as egg, larva, pupa, and adult. The pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pesticidally effective amount of the inventive mixtures or of compositions comprising the mixtures.

“Locus” means a plant, seed, soil, area, material or environment in which a pest is growing or may grow.

In general, “pesticidally effective amount” means the amount of the inventive mixtures or of compositions comprising the mixtures needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The pesticidally effective amount can vary for the various mixtures and/or compositions used in the invention. A pesticidally effective amount of the mixtures and/or compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.

The inventive compounds I or the inventive mixtures or compositions of these mixtures can also be employed for protecting plants from attack or infestation by invertebrate pests such as insects, acarids or nematodes comprising contacting a plant, or soil or water in which the plant is growing.

The inventive compounds or mixtures are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part) and through trophallaxis and transfer.

Preferred application methods are into water bodies, via soil, cracks and crevices, pastures, manure piles, sewers, into water, on floor, wall, or by perimeter spray application and bait.

According to another preferred embodiment of the invention, for use against non crop pests such as ants, termites, wasps, flies, mosquitoes, crickets, locusts, or cockroaches the inventive mixtures are prepared into a bait preparation.

The bait can be a liquid, a solid or a semisolid preparation (e.g. a gel). The bait employed in the composition is a product which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitoes, crickets etc. or cockroaches to eat it. This attractant may be chosen from feeding stimulants or para and/or sex pheromones readily known in the art.

Methods to control infectious diseases transmitted by insects (e.g. malaria, dengue and yellow fever, lymphatic filariasis, and leishmaniasis) with the inventive mixtures and their respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like. Insecticidal compositions for application to fibers, fabric, knitgoods, non-wovens, netting material or foils and tarpaulins preferably comprise a composition including the inventive mixtures, optionally a repellent and at least one binder.

The compounds according to the invention, compositions comprising them, the inventive mixtures and the compositions comprising them can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public facilities).

In the case of soil treatment or of application to the pests dwelling place or nest, the quantity of active ingredient(s) ranges from 0.0001 to 500 g per 100 m², preferably from 0.001 to 20 g per 100 m².

Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compound(s) per m² treated material, desirably from 0.1 g to 50 g per m².

Insecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and/or insecticide.

For use in bait compositions, the typical content of active ingredient(s) is from 0.0001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound. The composition used may also comprise other additives such as a solvent of the active material, a flavoring agent, a preserving agent, a dye or a bitter agent. Its attractiveness may also be enhanced by a special color, shape or texture.

For use in spray compositions, the content of the mixture of the active ingredients is from 0.001 to 80 weights %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.

For use in treating crop plants, the rate of application of the mixture of the active ingredients of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare.

In the context of the present invention, the term plant refers to an entire plant, a part of the plant or the plant propagation material.

The mixtures of the present invention and the compositions comprising them are particularly important in the control of a multitude of insects on various cultivated plants.

Plants which can be treated with the inventive mixtures include all genetically modified plants or transgenic plants, e.g. crops which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods, or plants which have modified characteristics in comparison with existing plants, which can be generated for example by traditional breeding methods and/or the generation of mutants, or by recombinant procedures.

The term “plant propagation material” is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be mentioned. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.

The term “cultivated plants” is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering. Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant.

The term “cultivated plants” is to be understood also including plants that have been rendered tolerant to applications of specific classes of herbicides, such as hydroxy-phenylpyruvate dioxygenase (HPPD) inhibitors; acetolactate synthase (ALS) inhibitors, such as sulfonyl ureas (see e.g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073) or imidazolinones (see e.g. U.S. Pat. No. 6,222,100, WO 01/82685, WO 00/26390, WO 97/41218, WO 98/02526, WO 98/02527, WO 04/106529, WO 05/20673, WO 03/14357, WO 03/13225, WO 03/14356, WO 04/16073); enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate (see e.g. WO 92/00377); glutamine synthetase (GS) inhibitors, such as glufosinate (see e.g. EP-A 242 236, EP-A 242 246) or oxynil herbicides (see e.g. U.S. Pat. No. 5,559,024) as a result of conventional methods of breeding or genetic engineering. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), for example Clearfield® summer rape (Canola) being tolerant to imidazolinones, e.g. imazamox. Genetic engineering methods have been used to render cultivated plants, such as soybean, cotton, corn, beets and rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).

The term “cultivated plants” is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as 6-endotoxins, e.g. CryIA(b), CryIA(c), CryIF, CryIF(a2), CryIIA(b), CryIIIA, CryIIIB(b1) or Cry9c; vegetative insecticidal proteins (VIP), e.g. VIP1, VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scorpion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilben synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, for example WO 02/015701). Further examples of such toxins or genetically-modified plants capable of synthesizing such toxins are disclosed, for example, in EP-A 374 753, WO 93/007278, WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/018810 und WO 03/052073. The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of insects, especially to beetles (Coeloptera), two-winged insects (Diptera), and butterflies (Lepidoptera).

The term “cultivated plants” is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called “pathogenesis-related proteins” (PR proteins, see, for example EP-A 392 225), plant disease resistance genes (for example potato cultivars, which express resistance genes acting against Phytophthora infestans derived from the mexican wild potato Solanum bulbocastanum) or T4-lyso-zynn (e.g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above.

The term “cultivated plants” is to be understood also including plants that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e.g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environ-mental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.

The term “cultivated plants” is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, for example oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e.g. Nexera® rape).

The term “cultivated plants” is to be understood also including plants that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, for example potatoes that produce increased amounts of amylopectin (e.g. Amflora® potato).

Some of the inventive mixtures have systemic action and can therefore be used for the protection of the plant shoot against foliar pests as well as for the treatment of the seed and roots against soil pests.

The mixtures according to the present invention are therefore suitable for the treatment of seeds in order to protect the seed from insect pest, in particular from soil-living insect pests and the resulting plants roots and shoots against soil pests and foliar insects.

The protection of the resulting plants roots and shoots is preferred.

More preferred is the protection of resulting plants shoots from piercing and sucking insects.

The present invention therefore comprises a method for the protection of seeds from insects, in particular from soil insects and of the seedlings roots and shoots from insects, in particular from soil and foliar insects, said method comprising contacting the seeds before sowing and/or after pregermination with mixtures according to the present invention. Particularly preferred is a method, wherein the plants roots and shoots are protected, more preferably a method, wherein the plants shoots are protected form piercing and sucking insects, most preferably a method, wherein the plants shoots are protected from aphids.

The term seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.

The term seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.

The present invention also comprises seeds coated with or containing the active compound(s). The term “coated with and/or containing” generally signifies that the active ingredient(s) are for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation products are (re)planted, it may absorb the active ingredient.

Suitable seeds are seeds of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize/sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.

In addition, the mixtures according to the invention may also be used for the treatment seeds from plants, which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods.

For example, the active mixtures can be employed in treatment of seeds from plants, which are resistant to herbicides from the group consisting of the sulfonylureas, imidazolinones, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances (see for example, EP-A 242 236, EP-A 242 246) (WO 92/00377) (EP-A 257 993, U.S. Pat. No. 5,013,659) or in transgenic crop plants, for example cotton, with the capability of producing Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A 142 924, EP-A 193 259).

Furthermore, the compounds of the invention and the mixtures according to the present invention can be used also for the treatment of seeds from plants, which have modified characteristics in comparison with existing plants consist, which can be generated for example by traditional breeding methods and/or the generation of mutants, or by recombinant procedures). For example, a number of cases have been described of recombinant modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827, WO 91/19806) or of transgenic crop plants having a modified fatty acid composition (WO91/13972).

The seed treatment application of the mixtures is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.

In the treatment of seeds the corresponding formulations are applied by treating the seeds with an effective amount of the mixture according to the present invention. Herein, the application rates of the active compound(s) are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 2.5 kg per 100 kg of seed. For specific crops such as lettuce the rate can be higher.

Compositions, which are especially useful for seed treatment are e.g.:

A Soluble concentrates (SL, LS)

D Emulsions (EW, EO, ES)

E Suspensions (SC, OD, FS)

F Water-dispersible granules and water-soluble granules (WG, SG)

G Water-dispersible powders and water-soluble powders (WP, SP, WS)

H Gel-Formulations (GF)

I Dustable powders (DP, DS)

Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter

In a preferred embodiment a FS formulation is used for seed treatment. Typically, a FS formulation may comprise 1-800 g/l of active ingredient(s), 1-200 g/I Surfactant, 0 to 200 g/I anti-freezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.

Preferred FS formulations of compounds of formula I for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/I) of the active ingredient(s), from 0.1 to 20% by weight (1 to 200 g/I) of at least one surfactant, e.g. 0.05 to 5% by weight of a wetter and from 0.5 to 15% by weight of a dispersing agent, up to 20% by weight, e.g. from 5 to 20% of an anti-freeze agent, from 0 to 15% by weight, e.g. 1 to 15% by weight of a pigment and/or a dye, from 0 to 40% by weight, e.g. 1 to 40% by weight of a binder (sticker/adhesion agent), optionally up to 5% by weight, e.g. from 0.1 to 5% by weight of a thickener, optionally from 0.1 to 2% of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1% by weight and a filler/vehicle up to 100% by weight.

Seed treatment formulations may additionally also comprise binders and optionally colorants.

Binders can be added to improve the adhesion of the active materials on the seeds after treatment. Suitable binders are block copolymers EO/PO surfactants but also polyvinylalcohols, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, polyethyleneimines (Lupasol®, Polynnin®), polyethers, polyurethans, polyvinylacetate, tylose and copolymers derived from these polymers.

Optionally, also colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodannin B, C.I. Pigment Red 112, C.I. Solvent Red 1, pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1, pigment blue 80, pigment yellow 1, pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1, pigment red 57:1, pigment red 53:1, pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

The invention also relates to seed comprising mixtures according to the present invention. The amount of the compound I or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed.

The mixtures of the present invention or the inventive compounds are in particular also suitable for being used for combating parasites in and on animals.

An object of the present invention is therefore also to provide new methods to control parasites in and on animals. Another object of the invention is to provide safer pesticides for animals. Another object of the invention is further to provide pesticides for animals that may be used in lower doses than existing pesticides. And another object of the invention is to provide pesticides for animals, which provide a long residual control of the parasites.

The invention also relates to compositions containing a parasiticidally effective amount of compounds of formula I or the enantiomers or veterinarily acceptable salts thereof and an acceptable carrier, for combating parasites in and on animals.

The present invention also provides a method for treating, controlling, preventing and protecting animals against infestation and infection by parasites, which comprises orally, topically or parenterally administering or applying to the animals a parasiticidally effective amount of mixture of the present invention or a composition comprising it or the inventive compound.

The invention also provides a process for the preparation of a composition for treating, controlling, preventing or protecting animals against infestation or infection by parasites which comprises a parasiticidally effective amount of a mixture of the present invention or a composition comprising it or a compound according to the invention.

Activity of compounds against agricultural pests does not suggest their suitability for control of endo- and ectoparasites in and on animals which requires, for example, low, non-emetic dosages in the case of oral application, metabolic compatibility with the animal, low toxicity, and a safe handling.

Surprisingly it has now been found that mixtures of the present invention are suitable for combating endo- and ectoparasites in and on animals. Surprisingly it has now been found that the inventive compounds I are suitable for combating endo- and ectoparasites in and on animals.

Inventive compounds or mixtures of the present invention and compositions comprising them are preferably used for controlling and preventing infestations and infections animals including warm-blooded animals (including humans) and fish. They are for example suitable for controlling and preventing infestations and infections in mammals such as cattle, sheep, swine, camels, deer, horses, pigs, poultry, rabbits, goats, dogs and cats, water buffalo, donkeys, fallow deer and reindeer, and also in fur-bearing animals such as mink, chinchilla and raccoon, birds such as hens, geese, turkeys and ducks and fish such as fresh- and salt-water fish such as trout, carp and eels.

Inventive compounds I, mixtures of the present invention and compositions comprising them are preferably used for controlling and preventing infestations and infections in domestic animals, such as dogs or cats.

Infestations in warm-blooded animals and fish include, but are not limited to, lice, biting lice, ticks, nasal bots, keds, biting flies, muscoid flies, flies, myiasitic fly larvae, chiggers, gnats, mosquitoes and fleas.

The inventive compounds, the mixtures of the present invention and compositions comprising them are suitable for systemic and/or non-systemic control of ecto- and/or endoparasites. They are active against all or some stages of development.

The mixtures of the present invention are especially useful for combating ectoparasites.

The mixture of the present invention is especially useful for combating parasites of the following orders and species, respectively:

-   -   fleas (Siphonaptera), e.g. Ctenocephalides felis,         Ctenocephalides canis, Xenopsylla cheopis, Pulex irritans, Tunga         penetrans, and Nosopsyllus fasciatus,

cockroaches (Blattaria-Blattodea), e.g. Blattella germanica, Blattella asahinae, Periplaneta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis.

flies, mosquitoes (Diptera), e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nignpalpus, Culex quinquefasciatus, Culex tarsalis, Culiseta inornata, Culiseta melanura, Dermatobia hominis, Fannia canicularis, Gasterophilus intestinalis, Glossina morsitans, Glossina palpalis, Glossina fuscipes, Glossina tachinoides, Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hypoderma lineata, Leptoconops torrens, Lucilia caprina, Lucilia cuprina, Lucilia sericata, Lycoria pectoralis, Mansonia spp., Musca domestica, Muscina stabulans, Oestrus ovis, Phlebotomus argentipes, Psorophora columbiae, Psorophora discolor, Prosimulium mixtum, Sarcophaga haemorrhoidalis Sarcophaga sp., Simulium vittatum, Stomoxys calcitrans, Tabanus bovinus, Tabanus atratus, Tabanus lineola, and Tabanus

lice (Phthiraptera), e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthirus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus.

ticks and parasitic mites (Parasitiformes): ticks (Ixodida), e.g. Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Rhiphicephalus sanguineus, Dermacentor andersoni, Dermacentor variabilis, Amblyomma americanum, Ambryomma maculatum, Ornithodorus hermsi, Ornithodorus turicata and parasitic mites (Mesostigmata), e.g. Ornithonyssus bacoti and Dermanyssus gallinae,

Actinedida (Prostigmata) und Acaridida (Astigmata) e.g. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., and Laminosioptes spp,

Bugs (Heteropterida): Cimex lectularius, Cimex hemipterus, Reduvius senilis, Triatoma spp., Rhodnius ssp., Panstrongylus ssp. and Arilus critatus,

Anoplurida, e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., and Solenopotes spp,

Mallophagida (suborders Arnblycerina and Ischnocerina), e.g. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Trichodectes spp., and Felicola spp,

Roundworms Nematoda:

Wipewornns and Trichinosis (Trichosyringida), e.g. Trichinellidae (Trichinella spp), (Trichuridae) Trichuris spp., Capillaria spp,

Rhabditida, e.g. Rhabditis spp, Strongyloides spp., Helicephalobus spp,

Strongylida, e.g. Strongylus spp., Ancylostoma spp., Necator americanus, Bunostomum spp. (Hookworm), Trichostrongylus spp., Haemonchus contortus., Ostertagia spp., Cooperia spp., Nematodirus spp., Dictyocaulus spp., Cyathostoma spp., Oesophagostomum spp., Stephanurus dentatus, Ollulanu spp., Chabertia spp., Stephanurus dentatus, Syngamus trachea, Ancylostoma spp., Uncinaria spp., Globocephalus spp., Necator spp., Metastrongylus spp., Muellerius capillaris, Protostrongylus spp., Angiostrongylus spp., Parelaphostrongylus spp. Aleurostrongylus abstrusus, and Dioctophyma renale,

Intestinal roundworms (Ascaridida), e.g. Ascaris lumbricoides, Ascaris suum, Ascaridia Parascaris equorum, Enterobius vermicularis (Threadworm), Toxocara canis, Toxascaris leonine, Skijabinema spp., and Oxyuris equi,

Camallanida, e.g. Dracunculus medinensis (guinea worm)

Spirurida, e.g. Thelazia spp. Wuchereria spp., Brugia spp., Onchocerca spp., Dirofilari spp. a, Dipetalonema spp., Setaria spp., Elaeophora spp., Spirocerca lupi, and Habronema spp.,

Thorny headed worms (Acanthocephala), e.g. Acanthocephalus spp., Macracanthorhynchus hirudinaceus and Oncicola spp,

Planarians (Plathelminthes):

Flukes (Trematoda), e.g. Faciola spp., Fascioloides magna, Paragonimus spp., Dicrocoelium spp., Fasciolopsis buski, Clonorchis sinensis, Schistosoma spp., Trichobilharzia spp., Alaria alata, Paragonimus spp., and Nanocyetes spp,

Cercomeromorpha, in particular Cestoda (Tapeworms), e.g. Diphyllobothrium spp., Tenia spp., Echinococcus spp., Dipylidium caninum, Multiceps spp., Hymenolepis spp., Mesocestoides spp., Vampirolepis spp., Moniezia spp., Anoplocephala spp., Sirometra spp., Anoplocephala spp., and Hymenolepis spp.

The compounds according to the invention, the mixtures of the present invention and compositions containing them are particularly useful for the control of pests from the orders Diptera, Siphonaptera and Ixodida.

Moreover, the use of compounds according to the invention, mixtures of the present invention and compositions containing them for combating mosquitoes is especially preferred.

The use of compounds according to the invention, mixtures of the present invention and compositions containing them for combating flies is a further preferred embodiment of the present invention.

Furthermore, the use of the compounds according to the invention, mixtures of the present invention and compositions containing them for combating fleas is especially preferred.

The use of compounds according to the invention, the mixtures of the present invention and compositions containing them for combating ticks is a further preferred embodiment of the present invention.

The mixtures of the present invention also are especially useful for combating endoparasites (roundworms nematoda, thorny headed worms and planarians).

Administration can be carried out both prophylactically and therapeutically.

Administration of the active compound(s) is carried out directly or in the form of suitable preparations, orally, topically/dermally or parenterally.

For oral administration to warm-blooded animals, the compound according to the invention, mixtures of the present invention may be formulated as animal feeds, animal feed premixes, animal feed concentrates, pills, solutions, pastes, suspensions, drenches, gels, tablets, boluses and capsules. In addition, the mixtures of the present invention may be administered to the animals in their drinking water. For oral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the formula I compound, preferably with 0.5 mg/kg to 100 mg/kg of animal body weight per day.

Alternatively, the compounds of the invention, mixtures of the present invention may be administered to animals parenterally, for example, by intraruminal, intramuscular, intravenous or subcutaneous injection. The formula I compounds may be dispersed or dissolved in a physiologically acceptable carrier for subcutaneous injection. Alternatively, the mixtures of the present invention may be formulated into an implant for subcutaneous administration. In addition the formula I compound may be transdermally administered to animals. For parenteral administration, the dosage form chosen should provide the animal with 0.01 mg/kg to 100 mg/kg of animal body weight per day of the active compounds.

The compounds according to the invention, mixtures of the present invention may also be applied topically to the animals in the form of dips, dusts, powders, collars, medallions, sprays, shampoos, spot-on and pour-on formulations and in ointments or oil-in-water or water-in-oil emulsions. For topical application, dips and sprays usually contain 0.5 ppm to 5,000 ppm and preferably 1 ppm to 3,000 ppm of the active compounds. In addition, the active compound mixtures may be formulated as ear tags for animals, particularly quadrupeds such as cattle and sheep.

Suitable preparations are:

-   -   Solutions such as oral solutions, concentrates for oral         administration after dilution, solutions for use on the skin or         in body cavities, pouring-on formulations, gels;     -   Emulsions and suspensions for oral or dermal administration;         semi-solid preparations;     -   Formulations in which the active compound is processed in an         ointment base or in an oil-in-water or water-in-oil emulsion         base;     -   Solid preparations such as powders, premixes or concentrates,         granules, pellets, tablets, boluses, capsules; aerosols and         inhalants, and active compound-containing shaped articles.

Compositions suitable for injection are prepared by dissolving the active ingredient in a suitable solvent and optionally adding further ingredients such as acids, bases, buffer salts, preservatives, and solubilizers. The solutions are filtered and filled sterile.

Suitable solvents are physiologically tolerable solvents such as water, alkanols such as ethanol, butanol, benzyl alcohol, glycerol, propylene glycol, polyethylene glycols, N-methyl-pyrrolidone, 2-pyrrolidone, and mixtures thereof.

The active compounds can optionally be dissolved in physiologically tolerable vegetable or synthetic oils which are suitable for injection.

Suitable solubilizers are solvents which promote the dissolution of the active compound in the main solvent or prevent its precipitation. Examples are polyvinylpyrrolidone, polyvinyl alcohol, polyoxyethylated castor oil, and polyoxyethylated sorbitan ester.

Suitable preservatives are benzyl alcohol, trichlorobutanol, p-hydroxybenzoic acid esters, and n-butanol.

Oral solutions are administered directly. Concentrates are administered orally after prior dilution to the use concentration. Oral solutions and concentrates are prepared according to the state of the art and as described above for injection solutions, sterile procedures not being necessary.

Solutions for use on the skin are trickled on, spread on, rubbed in, sprinkled on or sprayed on.

Solutions for use on the skin are prepared according to the state of the art and according to what is described above for injection solutions, sterile procedures not being necessary.

Further suitable solvents are polypropylene glycol, phenyl ethanol, phenoxy ethanol, ester such as ethyl or butyl acetate, benzyl benzoate, ethers such as alkyleneglycol alkylether, e.g. dipropylenglycol monomethylether, ketons such as acetone, methylethylketone, aromatic hydrocarbons, vegetable and synthetic oils, dimethylformamide, dimethylacetamide, transcutol, sol-ketal, propylencarbonate, and mixtures thereof.

It may be advantageous to add thickeners during preparation. Suitable thickeners are inorganic thickeners such as bentonites, colloidal silicic acid, aluminium monostearate, organic thickeners such as cellulose derivatives, polyvinyl alcohols and their copolymers, acrylates and methacrylates.

Gels are applied to or spread on the skin or introduced into body cavities. Gels are prepared by treating solutions which have been prepared as described in the case of the injection solutions with sufficient thickener that a clear material having an ointment-like consistency results.

The thickeners employed are the thickeners given above.

Pour-on formulations are poured or sprayed onto limited areas of the skin, the active compound penetrating the skin and acting systemically.

Pour-on formulations are prepared by dissolving, suspending or emulsifying the active compound in suitable skin-compatible solvents or solvent mixtures. If appropriate, other auxiliaries such as colorants, bioabsorption-promoting substances, antioxidants, light stabilizers, adhesives are added.

Suitable solvents which are: water, alkanols, glycols, polyethylene glycols, polypropylene glycols, glycerol, aromatic alcohols such as benzyl alcohol, phenylethanol, phenoxyethanol, esters such as ethyl acetate, butyl acetate, benzyl benzoate, ethers such as alkylene glycol alkyl ethers such as dipropylene glycol monomethyl ether, diethylene glycol mono-butyl ether, ketones such as acetone, methyl ethyl ketone, cyclic carbonates such as propylene carbonate, ethylene carbonate, aromatic and/or aliphatic hydrocarbons, vegetable or synthetic oils, DMF, dimethylacetamide, N-alkylpyrrolidones such as methylpyrrolidone, N-butylpyrrolidone or N-octylpyrrolidone, N-methylpyrrolidone, 2-pyrrolidone, 2,2-dimethyl-4-oxy-methylene-1,3-dioxolane and glycerol formal.

Suitable colorants are all colorants permitted for use on animals and which can be dissolved or suspended.

Suitable absorption-promoting substances are, for example, DMSO, spreading oils such as isopropyl myristate, dipropylene glycol pelargonate, silicone oils and copolymers thereof with polyethers, fatty acid esters, triglycerides, fatty alcohols.

Suitable antioxidants are sulfites or metabisulfites such as potassium metabisulfite, ascorbic acid, butylhydroxytoluene, butylhydroxyanisole, tocopherol.

Suitable light stabilizers are, for example, novantisolic acid.

Suitable adhesives are, for example, cellulose derivatives, starch derivatives, polyacrylates, natural polymers such as alginates, gelatin.

Emulsions can be administered orally, dermally or as injections.

Emulsions are either of the water-in-oil type or of the oil-in-water type.

They are prepared by dissolving the active compound either in the hydrophobic or in the hydrophilic phase and homogenizing this with the solvent of the other phase with the aid of suitable emulsifiers and, if appropriate, other auxiliaries such as colorants, absorption-promoting substances, preservatives, antioxidants, light stabilizers, viscosity-enhancing substances.

Suitable hydrophobic phases (oils) are:

liquid paraffins, silicone oils, natural vegetable oils such as sesame oil, almond oil, castor oil, synthetic triglycerides such as caprylic/capric biglyceride, triglyceride mixture with vegetable fatty acids of the chain length C₈-C₁₂ or other specially selected natural fatty acids, partial glyceride mixtures of saturated or unsaturated fatty acids possibly also containing hydroxyl groups, mono- and diglycerides of the C₈-C₁₀ fatty acids,

fatty acid esters such as ethyl stearate, di-n-butyryl adipate, hexyl laurate, dipropylene glycol perlargonate, esters of a branched fatty acid of medium chain length with saturated fatty alcohols of chain length C₁₆-C₁₈, isopropyl myristate, isopropyl palmitate, caprylic/capric acid esters of saturated fatty alcohols of chain length C₁₂-C₁₈, isopropyl stearate, oleyl oleate, decyl oleate, ethyl oleate, ethyl lactate, waxy fatty acid esters such as synthetic duck coccygeal gland fat, dibutyl phthalate, diisopropyl adipate, and ester mixtures related to the latter, fatty alcohols such as isotridecyl alcohol, 2-octyldodecanol, cetylstearyl alcohol, oleyl alcohol, and fatty acids such as oleic acid and mixtures thereof.

Suitable hydrophilic phases are: water, alcohols such as propylene glycol, glycerol, sorbitol and mixtures thereof.

Suitable emulsifiers are:

non-ionic surfactants, e.g. polyethoxylated castor oil, polyethoxylated sorbitan monooleate, sorbitan monostearate, glycerol monostearate, polyoxyethyl stearate, alkylphenol polyglycol ether;

ampholytic surfactants such as di-sodium N-lauryl-p-iminodipropionate or lecithin;

anionic surfactants, such as sodium lauryl sulfate, fatty alcohol ether sulfates, mono/dialkyl polyglycol ether orthophosphoric acid ester monoethanolamine salt;

cation-active surfactants, such as cetyltrimethylammonium chloride.

Suitable further auxiliaries are: substances which enhance the viscosity and stabilize the emulsion, such as carboxymethylcellulose, methylcellulose and other cellulose and starch derivatives, polyacrylates, alginates, gelatin, gum arabic, polyvinylpyrrolidone, polyvinyl alcohol, copolymers of methyl vinyl ether and maleic anhydride, polyethylene glycols, waxes, colloidal silicic acid or mixtures of the substances mentioned.

Suspensions can be administered orally or topically/dermally. They are prepared by suspending the active compound in a suspending agent, if appropriate with addition of other auxiliaries such as wetting agents, colorants, bioabsorption-promoting substances, preservatives, antioxidants, light stabilizers.

Liquid suspending agents are all homogeneous solvents and solvent mixtures.

Suitable wetting agents (dispersants) are the emulsifiers given above.

Other auxiliaries which may be mentioned are those given above.

Semi-solid preparations can be administered orally or topically/dermally. They differ from the suspensions and emulsions described above only by their higher viscosity.

For the production of solid preparations, the active compound(s) is mixed with suitable excipients, if appropriate with addition of auxiliaries, and brought into the desired form.

Suitable excipients are all physiologically tolerable solid inert substances. Those used are inorganic and organic substances. Inorganic substances are, for example, sodium chloride, carbonates such as calcium carbonate, hydrogencarbonates, aluminium oxides, titanium oxide, silicic acids, argillaceous earths, precipitated or colloidal silica, or phosphates. Organic substances are, for example, sugar, cellulose, foodstuffs and feeds such as milk powder, animal meal, grain meals and shreds, starches.

Suitable auxiliaries are preservatives, antioxidants, and/or colorants which have been mentioned above.

Other suitable auxiliaries are lubricants and glidants such as magnesium stearate, stearic acid, talc, bentonites, disintegration-promoting substances such as starch or crosslinked polyvinylpyrrolidone, binders such as starch, gelatin or linear polyvinylpyrrolidone, and dry binders such as microcrystalline cellulose.

In general, “parasiticidally effective amount” means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism. The parasiticidally effective amount can vary for the various compounds/compositions used in the invention. A parasiticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired parasiticidal effect and duration, target species, mode of application, and the like.

The compositions which can be used in the invention can comprise generally from about 0.001 to 95 wt % of the active compounds of the mixtures of the present invention.

Generally it is favorable to apply the active compounds of the mixtures of the present invention in total amounts of 0.5 mg/kg to 100 mg/kg per day, preferably 1 mg/kg to 50 mg/kg per day.

Ready-to-use preparations contain the active compounds of the mixtures of the present invention acting against parasites, preferably ectoparasites, in concentrations of 10 ppm to 80 percent by weight, preferably from 0.1 to 65 percent by weight, more preferably from 1 to 50 percent by weight, most preferably from 5 to 40 percent by weight.

Preparations which are diluted before use contain the active compounds of the mixtures of the present invention acting against ectoparasites in concentrations of 0.5 to 90 percent by weight, preferably of 1 to 50 percent by weight.

Furthermore, the preparations comprise the active compounds of the mixtures of the present invention against endoparasites in concentrations of 10 ppm to 2 percent by weight, preferably of 0.05 to 0.9 percent by weight, very particularly preferably of 0.005 to 0.25 percent by weight.

In a preferred embodiment of the present invention, the compositions comprising the mixtures of the present invention are applied dermally/topically.

In a further preferred embodiment, the topical application is conducted in the form of compound-containing shaped articles such as collars, medallions, ear tags, bands for fixing at body parts, and adhesive strips and foils.

Generally it is favorable to apply solid formulations which release the active compounds of the mixtures of the present invention in total amounts of 10 mg/kg to 300 mg/kg, preferably 20 mg/kg to 200 mg/kg, most preferably 25 mg/kg to 160 mg/kg body weight of the treated animal in the course of three weeks.

For the preparation of the shaped articles, thermoplastic and flexible plastics as well as elastomers and thermoplastic elastomers are used. Suitable plastics and elastomers are polyvinyl resins, polyurethane, polyacrylate, epoxy resins, cellulose, cellulose derivatives, polyamides and polyester which are sufficiently compatible with the compounds of formula I. A detailed list of plastics and elastomers as well as preparation procedures for the shaped articles is given e.g. in WO 03/086075.

EXAMPLES

The present invention is now illustrated in further details by the following examples, without imposing any limitation thereto.

Example 1 Preparation of N,5-dimethyl-N-pyridazin-4-yl-1-(1-spiro[2.2]pentan-5-ylethyl)pyrazole-4-carboxamide [I-22]

A solution of 594 mg 5-methyl-1-(1-spiro[2.2]pentan-5-ylethyl)pyrazole-4-carbonyl chloride in 5 mL THF was added dropwise to a solution of 271 mg N-methylpyridazin-4-amine and 315 mg triethylamine in 30 mL THF at 0° C. The mixture was stirred at 20-25° C. for about 20 h, the solvent was evaporated and the residue was diluted with 70 mL dichloromethane, washed with 2×10 mL water, dried over MgSO₄ and evaporated. Purification by flash chromatography (CH₂Cl₂/MeOH) gave 522 mg of the title compound. HPLC-MS: RT 0.842 min, m/z [MH]+ 312.2

Compounds can in general be characterized e.g. by coupled High Performance Liquid Chromatography/mass spectrometry (HPLC/MS), by ¹H-NMR and/or by their melting points.

Analytical HPLC column: Phenomenex Kinetex 1.7 μm XB-C18 100A; 50×2.1 mm; mobile

phase: A: water+0.1% trifluoroacetic acid (TFA); B: acetonitrile+0.1% TFA; gradient: 5-100% B in 1.50 minutes; 100% B 0.20 min; flow: 0.8-1.0 mL/min in 1.50 minutes at 60° C.

MS-method: ESI positive.

RT=HPLC retention time; m/z of the [M+H]+, [M+Na]+ or [M+K]+ peaks.

Further compounds examples of the present invention were prepared by analogy to the above described synthetic methods and the hereunder table illustrates, without imposing any limitation thereto, compounds examples of formula (I) including their corresponding characterization data:

SP1 and SP2 have the following meaning in the herunder Table:

SP1:

SP2:

wherein # denotes the bond to the skeleton of formula (I)

TABLE I Compounds of formula (I) numbered C-1 to C-32 and wherein R² is CH₃ and R⁵ is H: Physical data (HPLC-MS) No. R¹ R³ R⁴ RT [min] m/z [MH]⁺ C-1 CH₂CH₃ 1-OCH₃—cC₃H₄ CH₃ 0.766 330.0 C-2 CH₃ 1-OCH₃—cC₃H₄ CH₃ 0.703 313.3 C-3 H 1-OCH₃—cC₃H₄ CH₃ 0.727 302.0 C-4 CH₃ CF₂CH₃ CH₃ 0.760 310.2 C-5 CH₂CH₃ CF₂CH₃ CH₃ 0.813 324.3 C-6 H CF₂CH₃ CH₃ 0.762 296.2 C-7 H SP1 0.738 344.2 C-8 CH₃ SP1 0.728 358.3 C-9 CH₂CH₃ SP1 0.798 372.2 C-10 CH₃ —CH₂OCH₂OCH₂— 0.830 336.2 C-11 CH₃ SP2 0.715 330.2 C-12 H CF(CH₃)₂ CH₃ 0.755 292.1 C-13 CH₃ CF(CH₃)₂ CH₃ 0.750 306.2 C-14 CH₂CH₃ CF(CH₃)₂ CH₃ 0.811 320.2 C-15 CH₂CH₃ SP2 0.747 344.2 C-16 H SP2 0.705 316.1 C-17 CH₂CH₃ —CH₂OCH₂OCH₂— 0.662 318.2 C-18 H —CH₂OCH₂OCH₂— 0.629 290.1 C-19 CH₂OCH₃ CHFCH₃ CH₃ 0.766 322.2 C-20 CH₂OCH₂CH₃ CHFCH₃ CH₃ 0.797 336.3 C-21 H spiro[2.2]pentan-5-yl CH₃ 0.839 298.2 C-22 CH₃ spiro[2.2]pentan-5-yl CH₃ 0.842 312.2 C-23 CH₃ 5-cyanospiro[2.2]pentan-5-yl CH₃ 0.727 337.2 C-24 H 5-cyanospiro[2.2]pentan-5-yl CH₃ 0.726 323.2 C-25 CH₂CH₃ 5-cyanospiro[2.2]pentan-5-yl CH₃ 0.781 351.2 C-26 CH₂CH₃ spiro[2.2]pentan-5-yl CH₃ 0.924 326.2 C-27 H C(CH₃)₂OCH₃ CH₃ 0.773 304.1 C-28 CH₃ C(CH₃)₂OCH₃ CH₃ 0.771 318.2 C-29 CH₂CH₃ C(CH₃)₂OCH₃ CH₃ 0.781 351.2 C-30 H 2-(methoxymethyl)spiro[2.2]pentan-5-yl CH₃ 0.809 342.4 C-31 CH₃ 2-(methoxymethyl)spiro[2.2]pentan-5-yl CH₃ 0.819 356.2 C-32 CH₂CH₃ 2-(methoxymethyl)spiro[2.2]pentan-5-yl CH₃ 0.861 370.2

Synergism can be described as an interaction where the combined effect of two or more compounds is greater than the sum of the individual effects of each of the compounds.

The presence of a synergistic effect in terms of percent control or efficacy, between two mixing partners (X and Y) can be calculated using the Colby equation (Colby, S. R., 1967, Calculating Synergistic and Antagonistic Responses in Herbicide Combinations, Weeds, 15, 20-22):

$E = {X + Y - \frac{XY}{100}}$

When the observed combined control effect is greater than the expected combined control effect (E), then the combined effect is synergistic.

The following tests can demonstrate the control efficacy of compounds, mixtures or compositions of this invention on specific pests and fungi. However, the pest control protection afforded by the compounds, mixtures or compositions is not limited to these species. In certain instances, combinations of a compound of this invention with other invertebrate pest control compounds or agents are found to exhibit synergistic effects against certain important invertebrate pests and/or harmful fungi.

The expected efficacies of active compound mixtures were determined using Colby's formula [R. S. Colby, “Calculating synergistic and antagonistic responses of herbicide combinations”, Weeds 15, 20-22 (1967)] and compared with the observed efficacies.

B.1 Cowpea Aphid (Aphis craccivora)

The active compounds were formulated in 50:50 (vol:vol) acetone:water. The test solution was prepared at the day of use. Potted cowpea plants colonized with 100-150 aphids of various stages were sprayed after the pest population had been recorded. Population reduction was assessed after 24, 72, and 120 hours.

In this test, the compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-21, C-22, C-23, C-24, C-25, C-26, C-27, C-28, and C-29 respectively at 500 ppm showed at least 75% mortality in comparison with untreated controls.

B.2 Cotton Aphid (Aphis gossypii, Mixed Life Stages)

The active compounds were formulated in cyclohexanone as a 10,0000 ppm solution supplied in 1.3 ml ABgene® tubes. These tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone: 50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v).

Cotton plants at the cotyledon stage were infested with aphids prior to treatment by placing a heavily infested leaf from the main aphid colony on top of each cotyledon. Aphids were allowed to transfer overnight to accomplish an infestation of 80-100 by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood, removed from the sprayer, and then maintained in a growth room under fluorescent lighting in a 24-hr photoperiod at 25° C. and 20-40% relative humidity. Aphid mortality on the treated plants, relative to mortality on untreated control plants, was determined after 5 days.

In this test, the compounds C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, and C-10 respectively at 10 ppm showed at least 75% mortality in comparison with untreated controls.

B.3 Silverleaf Whitefly (Bemisia argentifolii, Adult)

The active compounds were formulated in cyclohexanone as a 10,0000 ppm solution supplied in 1.3 ml ABgene® tubes. These tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone: 50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v).

Cotton plants at the cotyledon stage (one plant per pot) were sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood and then removed from the sprayer. Each pot was placed into a plastic cup and 10 to 12 whitefly adults (approximately 3-5 days old) were introduced. The insects were collected using an aspirator and 0.6 cm, nontoxic Tygon® tubing (R-3603) connected to a barrier pipette tip. The tip, containing the collected insects, was then gently inserted into the soil containing the treated plant, allowing insects to crawl out of the tip to reach the foliage for feeding. Cups were covered with a reusable screened lid (150-micron mesh polyester screen PeCap from Tetko, Inc.). Test plants were maintained in a growth room at 25° C. and 20-40% relative humidity for 3 days, avoiding direct exposure to fluorescent light (24 hour photoperiod) to prevent trapping of heat inside the cup. Mortality was assessed 3 days after treatment, compared to untreated control plants.

In this test, the C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, and C-9 respectively at 10 ppm showed at least 75% mortality in comparison with untreated controls.

B.4 Vetch Aphid (Megoura viciae)

The active compounds were formulated in 1:3 (vol:vol) DMSO: water with different concentrations of formulated compounds.

Bean leaf disks were placed into microtiterplates filled with 0.8% agar-agar and 2.5 ppm OPUS™. The leaf disks were sprayed with 2.5 μl of the test solution and 5 to 8 adult aphids were placed into the microtiter plates which were then closed and kept at 23±1° C. and 50±5% relative humidity under fluorescent light for 6 days. Mortality was assessed on the basis of vital, reproduced aphids. Aphid mortality and fecundity was then visually assessed.

In this test, the compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, C-10, C-11, C-12, C-13, C-14, C-15, C-16, C-17, C-18, C-19, C-21, C-22, C-23, C-24, C-25, C-26, C-27, C-28, C-29, C-30, C-31, and C-32 respectively at 2500 ppm showed at least 75% mortality in comparison with untreated controls.

B.5 Green Peach Aphid (Myzus persicae)

The active compounds were formulated in cyclohexanone as a 10,0000 ppm solution supplied in 1.3 ml ABgene® tubes. These tubes were inserted into an automated electrostatic sprayer equipped with an atomizing nozzle and they served as stock solutions for which lower dilutions were made in 50% acetone: 50% water (v/v). A nonionic surfactant (Kinetic®) was included in the solution at a volume of 0.01% (v/v).

Bell pepper plants at the first true-leaf stage were infested prior to treatment by placing heavily infested leaves from the main colony on top of the treatment plants. Aphids were allowed to transfer overnight to accomplish an infestation of 30-50 aphids per plant and the host leaves were removed. The infested plants were then sprayed by an automated electrostatic plant sprayer equipped with an atomizing spray nozzle. The plants were dried in the sprayer fume hood, removed, and then maintained in a growth room under fluorescent lighting in a 24 hour photoperiod at 25° C. and 20-40% relative humidity. Aphid mortality on the treated plants, relative to mortality on untreated control plants, was determined after 5 days.

In this test, compounds C-1, C-2, C-3, C-4, C-5, C-6, C-7, C-8, C-9, and C-10 respectively at 10 ppm showed at least 75% mortality in comparison with untreated controls.

B.7 Rice Plant Hopper (Nilaparvata lugens)

Rice seedlings were cleaned and washed 24 hours before spraying. The active compounds were formulated in 50:50 acetone: water and 0.1% vol/vol surfactant (EL 620) was added. Potted rice seedlings were sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants were kept at 28-29° C. and relative humidity of 50-60%. Percent mortality was recorded after 72 hours. In this test, C-10, and C-15 respectively at 500 ppm showed 75% mortality in comparison with untreated controls.

B.8 Orchid Thrips (Dichronnothrips corbetti)

The active compounds were formulated as a 50:50 (vol:vol) acetone:water solution. Surfactant (Alkannuls EL 620) was added at the rate of 0.1% (vol/vol). Vanda orchids petals were cleaned, washed and air dried prior to spraying. Petals were dipped into the test solution for 3 seconds, air dried, placed inside a resealable plastic and inoculated with 20 adults. The treated petals were kept inside the holding room at 28-29° C. and relative humidity of 50-60%. Percent mortality was recorded after 72 hours.

In this test, compounds C-4, C-5, and C-9 at 500 ppm showed at least 75% mortality in comparison with untreated controls.

B.9 Rice Green Leafhopper (Nephotettix virescens)

Rice seedlings were cleaned and washed 24 hours before spraying. The active compounds were formulated in 50:50 acetone: water, and 0.1% vol/vol surfactant (EL 620) was added. Potted rice seedlings were sprayed with 5 ml test solution, air dried, placed in cages and inoculated with 10 adults. Treated rice plants were kept at 28-29° C. and relative humidity of 50-60%. Percent mortality was recorded after 72 hours.

In this test, compound C-26 at 500 ppm showed at least 75% mortality in comparison with untreated controls.

Test 1—Control of vetch aphid

For evaluating control of vetch aphid (Megoura viciae) through contact or systemic means the test unit consisted of 24-well-microtiter plates containing broad bean leaf disks.

The compounds or mixtures were formulated using a solution containing 75% water and 25% Dimethylsulfoxide (DMSO). Different concentrations of formulated compounds or mixtures were sprayed onto the leaf disks at 2.5 μl, using a custom built micro atomizer, at two replications.

For experimental mixtures in these tests identical volumes of both mixing partners at the desired concentrations respectively, were mixed together.

After application, the leaf disks were air-dried and 5-8 adult aphids placed on the leaf disks inside the microtiter plate wells. The aphids were then allowed to suck on the treated leaf disks and incubated at 23+1° C., 50+5% relative humidity (RH) for 5 days. Aphid mortality and fecundity was then visually assessed.

Test 2—Control of Green Peach Aphid

For evaluating control of green peach aphid (Myzus persicae) through systemic means the test unit consisted of 96-well-microtiter plates containing liquid artificial diet under an artificial membrane.

The compounds or mixtures were formulated using a solution containing 75% water and 25% DMSO. Different concentrations of formulated compounds or mixtures were pipetted into the aphid diet, using a custom built pipetter, at two replications.

For experimental mixtures in these tests identical volumes of both mixing partners at the desired concentrations respectively, were mixed together.

After application, 5-8 adult aphids were placed on the artificial membrane inside the microtiter plate wells. The aphids were then allowed to suck on the treated aphid diet and incubated at 23+1° C., 50+5% RH for 3 days. Aphid mortality and fecundity was then visually assessed.

Test 3—Control of Boll Weevil

For evaluating control of boll weevil (Anthonomus grandis) the test unit consisted of 24-well-microtiter plates containing an insect diet and 20-30 A. grandis eggs. The compounds or mixtures were formulated using a solution containing 75% water and 25% DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 20 μl, using a custom built micro atomizer, at two replications.

For experimental mixtures in these tests identical volumes of both mixing partners at the desired concentrations respectively, were mixed together.

After application, microtiter plates were incubated at 23+1° C., 50+5% RH for 5 days. Egg and larval mortality was then visually assessed.

In this test, compounds C-4, C-5, C-6, C-22, C-25, and C-26 respectively at 2500 ppm showed at least 75% mortality in comparison with untreated controls.

Test 4—Control of Mediterranean fruitfly

For evaluating control of Mediterranean fruitfly (Ceratitis capitata) the test unit consisted of 96-well-microtiter plates containing an insect diet and 50-80 C. capitata eggs.

The compounds or mixtures were formulated using a solution containing 75% water and 25% DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 5 μl, using a custom built micro atomizer, at two replications.

For experimental mixtures in these tests identical volumes of both mixing partners at the desired concentrations respectively, were mixed together.

After application, microtiter plates were incubated at 28+1° C., 80+5% RH for 5 days. Egg and larval mortality was then visually assessed.

Test 5—Control of Tobacco Budworm

For evaluating control of tobacco budworm (Heliothis virescens) the test unit consisted of 96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs.

The compounds or mixtures were formulated using a solution containing 75% water and 25% DMSO. Different concentrations of formulated compounds or mixtures were sprayed onto the insect diet at 10 μl, using a custom built micro atomizer, at two replications.

For experimental mixtures in these tests identical volumes of both mixing partners at the desired concentrations respectively, were mixed together.

After application, microtiter plates were incubated at 28+1° C., 80+5% RH for 5 days. Egg and larval mortality was then visually assessed.

Tests 6 to 9: Microtests

The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.

The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds. These percentages were converted into efficacies.

Test 6—Activity Against the Grey Mold Botrytis cinerea in the Microtiterplate Test

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Botrci cinerea in an aqueous biomalt solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18° C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.

Test 7—Activity Against Rice Blast Pyricularia Oryzae in the Microtiterplate Test

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Pyricularia oryzae in an aqueous biomalt solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18° C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculatio

Test 8—Activity Against Early Blight on Tomatoes Caused by Alternaria solani

Microtest: the active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Alternaria solani in an aqueous biomalt solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18° C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation. The evaluation as described in Test 8 was made to give the following results:

Calculated Active efficacy compound/ Concentration Observed according active mixture (ppm) Mixture efficacy to Colby (%) I-674 63 — 1 I-698 63 — 3 1 — 7 I-680 63 — 3 Pyraclostrobin 0.016 — 16 Triticonazol 0.063 — 27 Fludioxonil 0.063 — 26 I-674 + 63 4000:1 62 17 Pyraclostrobin 0.016 I-698 + 1  16:1 56 32 Triticonazol 0.063 I-698 + 63 1000:1 54 28 Fludioxonil 0.063 I-680 + 63 1000:1 52 28 Fludioxonil 0.063

Test 9—Activity Against Leaf Blotch on Wheat Caused by Septoria tritici

The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Septoria tritici in an aqueous bionnalt solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18° C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.

Test 10 Control of Rhizoctonia solani

The compounds were dissolved in Acetone. Seeds of corn were treated in a treater as standard equipment. The products and concentrations are listed below. After the treatment the seeds were sown in pots, and rye seeds (infected with Rhizoctonia solani) were placed next to the seeds (1 seed per corn seed).

After cultivation in the greenhouse for 14 days at 20° C. and a relative humidity of 70% the plant height of the plants were measured.

The evaluation as described in Test 8 was made to give the following results:

Calculated Active Concentration efficacy compound/ (g a.i./100 kg Observed according active mixture seeds) Mixture efficacy (%) to Colby (%) I-674 63 — 5 I-698 250 — 3 I-680 63 — 0 Pyraclostrobin 63 — 49 Triticonazol 16 — 20 Fluxapyroxad 4 — 74 Mefenoxam 63 — 0 I-674 + 63 1:1 74 51 Pyraclostrobin 63 I-698 + 250 16:1  38 23 Triticonazol 16 I-698 + 250 63:1  93 75 Fluxapyroxad 4 I-680 + 63 1:1 18 0 Mefenoxam 63

Test 11—Control of Brown Rust on Wheat Caused by Puccinia recondite

Seeds of wheat were treated in a treater as standard equipment. The products and concentrations are listed below. At the same day the plants were seeded in pots. 14 days later at 19° C. and 70% humidity the plants were inoculated with spores of Puccinia recondite. To ensure the success the artificial inoculation, the plants were transferred to a humid chamber without light and a relative humidity of 95 to 99% and 20 to 24° C. for 24 h. Then the trial plants were cultivated for 6 days in a greenhouse chamber at 20-24° C. and a relative humidity between 65 and 70%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

Calculated Active Concentration efficacy compound/ (g a.i./100 kg Observed according active mixture seeds) Mixture efficacy (%) to Colby (%) Untreated 90% Disease I-674 250 — 0 I-698 63 — 4 I-680 250 — 0 Triticonazol 16 — 49 Fluxapyroxad 1 — 16 I-674 + 250 16:1 92 49 Triticonazol 16 I-698 + 63 63:1 44 20 Fluxapyroxad 1 I-680 + 250 16:1 69 49 Triticonazole 16

Test 12—Control of Powdery Mildew on Wheat Caused by Blumeria graminis f. Sp. Tritici

Seeds of wheat were treated in a treater as standard equipment. The products and concentrations are listed below. At the same day the plants were seeded in pots. 14 days later at 19° C. and 70% humidity the plants were inoculated with spores of Blumeria graminis f. sp. tritici (=syn. Elysiphe garminis f. sp. tritici) by shaking heavily infestated stock plants over the treated pots. After cultivation in the greenhouse for 7 days at 22-26° C. and a relative humidity between 60 to 90% the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

The evaluation as described in Test 8 was made to give the following results:

Calculated Active Concentration efficacy compound/ (g a.i./100 kg Observed according to active mixture seeds) Mixture efficacy (%) Colby (%) Untreated 82% Disease I-674 250 — 21 4 — 9 I-698 250 — 15 I-680 250 — 15 Thiabendazol 250 — 2 Mefenoxam 4 — 0 Triticonazol 16 — 60 I-674 + 250 1:1 51 23 Thiabendazol 250 I-674 + 4 1:1 33 9 Mefenoxam 4 I-698 + 250 1:1 51 17 Thiabendazol 250 I-698 + 250 63:1  94 66 Triticonazol 16 I-680 + 250 63:1  92 66 Triticonazol 16

Test 13—Activity Against Greenbug Aphid, Schizaphis graminum:

Wheat Seed Treatment

Technical material was dissolved in acetone at sub-lethal doses. 50 μL of solution was added to a 20-ml scintillation vial, 15 wheat seeds were added, and the seeds were coated by vortexing the vial for 1 minute. The seeds were allowed to dry and planted later the same day. Seeds were planted individually in a moistened, fertilized soil mixture of 1:1 North Carolina loamy sand (Sandhill soil):play sand in 40.32 cm² pots. Pots were arranged in a randomized complete block design in the greenhouse and top-watered daily. Plant emergence and shoot phytotoxicity were evaluated 4, 7, and 14 days after treatment (DAT). At 14 DAT (true leaf stage), each plant was infested with 10 greenbug aphids (Schizaphis graminum) of mixed stages. Plants were maintained on light carts in a randomized complete block design and bottom-watered as needed. Twelve replicates (pots) were prepared for plant emergence and five replicates were prepared for infestation. Live aphids were counted 4 DAI and the mean percent population reduction relative to the solvent blank control was calculated.

The evaluation as described in Test 8 was made to give the following results:

Activity with Insecticides of the Group A.1 to A.17:

Calculated Con- efficacy Active centration (g Observed according compound/active a.i./100 kg efficacy to mixture seeds) Mixture (%) Colby (%) I-674 33.7 — 28 I-698 150 — 74 I-680 2.9 — 23 Clothianidin 3.7 — 38 Cyantraniliprole 75 — 36 Fipronil 75 24 Imidacloprid 1.2 32 Thiamethoxam 4.4 16 chloranthraniliprole 75 30 I-680 + 2.9 1:2.3  64 52 Clothianidin 3.7 I-674 + 33.7:75 1:2.2  66 54 Cyantraniliprole I-680 + 2.9 1:25.9 45 41 Fipronil 75 I-698 + 150 125:1    87 82 Imidacloprid 1.2 I-680 + 2.9 2.4:1   50 47 Imidacloprid 1.2 I-698+ 150 34:1    82 78 Thiamethoxam 4.4 I-680 + 2.9 1:25.9 59 46 chloranthraniliprole 75

Activity with Fungicides of the Groups F.1 to F.11:

Concentration Calculated Active (g efficacy compound/ a.i./100 kg Observed according to active mixture seeds) Mixture efficacy (%) Colby (%) I-674 33.7 — 21 I-698 150 — 51 I-680 2.9 — 7 Fludioxonil 5 — 3 Fluxapyroxad 20 — 0 Mefenoxam 15 6 Pyraclostrobin 20 0 Thiabendazole 20 13 Triticonazole 5 7 I-680 + 2.9:5 1:1.7 12 10 Fludioxonil I-698 + 150 2:1   62 50 Fluxapyroxad 75 I-680 + 2.9 1:5.2 30 12 Mefenoxam 15 I-698 + 150 7.5:1   65 44 Pyraclostrobin 20 I-674+ 33.7 1.7:1   46 32 Thiabendazole 20 I-680 + 2.9 1:1.9 21 14 Triticonazole 5 

1. (canceled)
 2. A pesticidal mixture comprising as active compounds 1) at least one pyrazole compound A selected from the compound of formula I:

wherein R¹ is H, C₁-C₂-alkyl, or C₁-C₂-alkoxymethyl; R² is CH₃, CHF₂, or CF₃; R³ is selected from CN, C₂H₅, CH(CH₃)₂, CHF₂, CH₂F, CF₃, CH₂OCH₃, c-C₃H₅, 1-F-c-C₃H₄, 1-CN-c-C₃H₄, 1-CH₃-c-C₃H₄, 1-OCH₃-c-C₃H₄, 1-CF₃-c-C₃H₄, 1-OCF₃-c-C₃H₄, 1-SCH₃-c-C₃H₄, 1-SCF₃-c-C₃H₄, C(CH₃)₃, CF(CH₃)₂, C(CN)(CH₃)₂, C(OCH₃)(CH₃)₂, C(OCF₃)(CH₃)₂, C(SCH₃)(CH₃)₂, C(SCF₃)(CH₃)₂, C(CH₃)₂CF₃, CHFCH₃, CH(CN)CH₃, CF₂CH₃, C(OCH₃)₂CH₃, CH(OCH₃)CH₃, CH(OCF₃)CH₃, CH(SCH₃)CH₃, CH(SCF₃)CH₃, CH(CH₃)CF₃, CH₂SCH₃, CH₂SCF₃, CH₂OCF₃, CH₂CN, and CH₂CF₃; R⁴ is CH₃, C₂H₅, CHF₂, or CF₃; R⁵ is H, F, CN, CH₃, OCH₃, SCH₃, CF₃, OCF₃, or SCF₃; the stereoisomers, salts, tautomers and N-oxides thereof; and 2) at least one further compound B selected from the compounds of the following groups A.2, A.3, A.4, A.5, A.8, A.10, A.13, A.17, F.1, F.2, F.3, F.4, F.6, F.7, and F.8: A.2 Pyrethroid compounds, selected from the group consisting of acrinathrin, bifenthrin, cyfluthrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, flucythrinate, tau-fluvalinate, silafluofen, tralomethrin; A.3 Nicotinic receptor agonists/antagonists compounds, selected from the group consisting of acetamiprid, bensultap, cartap hydrochloride, clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, spinosad (allosteric agonist), spinetoram (allosteric agonist), thiacloprid, thiocyclam and thiosultap-sodium; A.4 GABA gated chloride channel antagonist compounds, selected from the group consisting of ethiprole and fipronil; A.5 Chloride channel activators, selected from the group consisting of abamectin, emamectin benzoate, and lepimectin; A.8 Selective feeding blockers, selected from the group consisting of pymetrozine and flonicamid; A.10 Lipid biosynthesis inhibitors, selected from the group consisting of spiromesifen and spirotetramat; A.13 Anthranilamide compounds, selected from the group consisting of chloranthraniliprole, cyantraniliprole; A.17 Various compounds, selected from the group consisting of pyrifluquinazon, sulfoxaflor, and afidopyropen; F.1 Respiration inhibitors selected from the following groups a), b), c) and d): a) Inhibitors of complex III at Qo site (e.g. strobilurins), selected from the group consisting of azoxystrobin, fluoxastrobin, picoxystrobin, pyraclostrobin, and trifloxystrobin; c) inhibitors of complex II (e.g. carboxamides), selected from the group consisting of boscalid, fluopyram, fluxapyroxad, penthiopyrad, and sedaxane; d) other respiration inhibitors (e.g. complex I, uncouplers), selected from the group consisting of ametoctradin; and silthiofam; F.2 Sterol biosynthesis inhibitors (SBI fungicides) selected from the following groups a), b) and c): a) C14 demethylase inhibitors (DMI fungicides), selected from the group consisting of the following triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, oxpoconazole, paclobutrazole, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole and uniconazole; the following imidazoles: imazalil, pefurazoate, prochloraz and triflumizol; and the following pyrimidines, pyridines and piperazines: fenarimol, nuarimol, pyrifenox and triforine; c) Inhibitors of 3-keto reductase: fenhexamid; F.3 Nucleic acid synthesis inhibitors selected from the following groups a) and b): a) phenylamides or acyl amino acid fungicides, selected from the group consisting of metalaxyl, and metalaxyl-M (mefenoxam); F.4 Inhibitors of cell division and cytoskeleton selected from the following groups a) and b): a) tubulin inhibitors, selected from the group consisting of benzimidazoles or thiophanates such as benomyl, carbendazim, fuberidazole, thiabendazole or thiophanate-methyl; and triazolopyrimidines such as 5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1,2,4]triazolo[1,5-a]pyrimidine; F.6 Signal transduction inhibitors selected from the following group: MAP/histidine kinase inhibitors, selected from the group consisting of fluoroimid, iprodione, procymidone, vinclozolin, fenpiclonil and fludioxonil; F.7 Lipid and membrane synthesis inhibitors selected from the following group: compounds affecting phospholipid biosynthesis and cell wall deposition, selected from the group consisting of dimethomorph, flumorph, mandipropamid, pyrimorph, benthiavalicarb, iprovalicarb, valifenalate and N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4-fluorophenyl) ester; F.8 Inhibitors with multi-site action selected from the following groups b), c) and d): b) thio- and dithiocarbamates selected from the group consisting of ferbam, mancozeb, maneb, metam, metiram, propineb, thiram, zineb and ziram; c) organochlorine compound chlorothalonil; d) guanidines and others selected from the group consisting of guanidine, dodine, dodine free base, guazatine, guazatine-acetate, iminoctadine, iminoctadine-triacetate, iminoctadine-tris(albesilate) and dithianon; comprising the pyrazole compound A and the active compound B in a weight ratio of from 500:1 to 1:100, except for pesticidal mixtures comprising a pyrazole compound of formula I, wherein R¹ is H, CH₃, C₂H₅, or CH₂OCH₃; R² is CH₃, CHF₂, or CF₃; R³ is CF₃, or c-C₃H₅; R⁴ is CH₃; and R⁵ is H.
 3. The mixture of claim 2, where in formula I the variable R¹ is CH₃, or C₂H₅.
 4. The mixture of claim 2, wherein the compound of formula I the variables R³, R⁴ and R⁵ have the following meanings: R³ is CN, CH(CH₃)₂, CHF₂, CH₂OCH₃, cyclopropyl, 1-F-cyclopropyl or 1-CN-cyclopropyl, R⁴ is CHF₂, R⁵ is H, or CH₃; stereoisomers, salts, tautomers and N-oxides thereof.
 5. The mixture of claim 2, wherein the compound of formula I the variables R¹, R², R³, R⁴ and R⁵ have the following meanings: R¹ is CH₃ or C₂H₅; R² is CH₃; R³ is CH(CH₃)₂, CHF₂, 1-CN-c-C₃H₄, CH₂CHF₂, CH₂CF₃, C(CN)(CH₃)₂, or CHFCH₃; R⁴ is CH₃, and R⁵ is H or CN.
 6. The mixture of claim 2, where the compound of formula I is selected from the compounds of the following table: No. R¹ R² R³ R⁴ R⁵ I-673 CH₃ CH₃ CH(CH₃)₂ CH₃ H I-674 CH₂CH₃ CH₃ CH(CH₃)₂ CH₃ H I-680 CH₂CH₃ CH₃ CHF₂ CH₃ H I-698 CH₂CH₃ CH₃ 1-CN—c-C₃H₄ CH₃ H


7. The mixture of claim 2 comprising a compound of formula I and a compound B from the groups A.2 to A.17.
 8. The mixture of claim 2 comprising a compound of formula I and a compound B from the groups F.1 to F.8.
 9. The mixture of claim 2, wherein at least one active compound B is selected from the group consisting of acrinathrin, bifenthrin, cyfluthrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, zeta-cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropathrin, flucythrinate, tau-fluvalinate, silafluofen, tralomethrin, acetamiprid, clothianidin, dinotefuran, imidacloprid, thiamethoxam, nitenpyram, thiacloprid, ethiprole, fipronil, abamectin, emamectin benzoate, lepimectin, flonicamid, pymetrozine; spiromesifen, spirotetramat, chloranthraniliprole, cyantraniliprole, pyrifluquinazon, sulfoxaflor, afidopyropen, azoxystrobin, pyraclostrobin, trifloxystrobin, fluoxastrobin, picoxystrobin, boscalid, fluopyram, fluxapyroxad, penthiopyrad, sedaxane, silthiofam, ametoctradin, difenoconazol, epoxiconazole, fluquinconazole, ipconazole, prothioconazole, tebuconazole, triticonazole, prochloraz, fenhexamid, metalaxyl, metalaxyl-M, carbendazim, thiophanate-methyl, iprodione, iprovalicarb, thiram, benthiavalicarb, mancozeb, and chlorothalonil.
 10. The mixture of claim 2, wherein the at least one active compound B is selected from fipronil, alpha-cypermethrin, thiamethoxam, abamectin, spirotetramat, imidacloprid, flonicamid, chloranthraniliprole, pymetrozine, sulfoxaflor and afidopyropen.
 11. The mixture of claim 2, wherein the at least one active compound B is selected from azoxystrobin, fluoxastrobin, picoxystrobin, pyraclostrobin, trifloxystrobin, fluxapyroxad, benthiavalicarb, iprovalicarb, fenhexamid, boscalid, mancozeb, ametoctradin, metalalxyl-m, carbendazim, iprodione, prochloraz, chlorothalonil, penthiopyrad, difenoconazole, epoxiconazole, ipconazole, prothioconazole and tebuconazole.
 12. A composition comprising a pesticidal mixture according to claim 2 and at least one inert liquid and/or solid carrier.
 13. An agricultural composition for combating animal pests comprising a pesticidal mixture according to claim 2 and at least one inert liquid and/or solid acceptable carrier and, if desired, at least one surfactant.
 14. A method for combating or controlling invertebrate pests comprising contacting the pest or its food supply, habitat or breeding grounds with a pesticidally effective amount of a pesticidal mixture according to claim
 2. 15. A method for protecting growing plants or plant propagation materials from attack or infestation by invertebrate pests comprising contacting a plant, a plant propagation material or soil or water in which the plant is growing, with a pesticidally effective amount of a pesticidal mixture according to claim
 2. 16. Plant propagation material comprising a pesticidal mixture according to claim 2 in an amount of from 0.1 g to 10 kg per 100 kg of seed.
 17. A method for protection of plant propagation material comprising contacting the plant propagation material with a pesticidal mixture according to claim 2 in an amount of from 0.1 g to 10 kg per 100 kg of plant propagation material.
 18. A method for controlling phytopathogenic harmful fungi, wherein the fungi, their habitat or the plants to be protected against fungal attack, the soil or seed are treated with an effective amount of a pesticidal mixture according to claim 2, wherein the at least one further compound B selected from the compounds of the groups F.1, F.2, F.3, F.4, F.6, F.7, and F.8.
 19. A method for protecting plants from phytopathogenic harmful fungi, wherein the fungi, their habitat or the plants to be protected against fungal attack, the soil or seed are treated with an effective amount of a pesticidal mixture according to claim 2, wherein the at least one further compound B selected from the compounds of the groups F.1, F.2, F.3, F.4, F.6, F.7, and F.8. 